NPASS Compound

Structure

CID130520 OpenBabel06191715492D 33 37 0 0 1 0 0 0 0 0999 V2000 -5.0594 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5034 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 -0.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9902 -0.6173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 4 27 1 0 0 0 0 6 7 1 0 0 0 0 6 19 2 0 0 0 0 7 22 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 26 1 0 0 0 0 17 30 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 29 1 6 0 0 0 21 25 1 1 0 0 0 21 26 1 0 0 0 0 22 25 1 1 0 0 0 22 28 1 0 0 0 0 23 26 1 1 0 0 0 23 31 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 27 28 1 1 0 0 0 28 5 1 1 0 0 0 29 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.32
Volume:	494.609
LogP:	4.048
LogD:	3.607
LogS:	-4.124
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	4.925
Fsp3:	0.828
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.509
MDCK Permeability:	6.683377705485327e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.576

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.862
Plasma Protein Binding (PPB):	82.1705551147461%
Volume Distribution (VD):	0.537
Pgp-substrate:	13.913347244262695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	2.616
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.487
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.115
Carcinogencity:	0.367
Eye Corrosion:	0.12
Eye Irritation:	0.19
Respiratory Toxicity:	0.983

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC130520

Natural Product ID:	NPC130520
*Common Name:**	30-Norhederagenin
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-6a,6b,9,12a-tetramethyl-2-methylidene-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	30-Norhederagenin
Standard InCHIKey:	FKUBIEWSGBVADJ-VZBPFLCRSA-N
Standard InCHI:	InChI=1S/C29H44O4/c1-18-8-13-29(24(32)33)15-14-27(4)19(20(29)16-18)6-7-22-25(2)11-10-23(31)26(3,17-30)21(25)9-12-28(22,27)5/h6,20-23,30-31H,1,7-17H2,2-5H3,(H,32,33)/t20-,21+,22+,23-,25-,26-,27+,28+,29-/m0/s1
SMILES:	OC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(=C)CC1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081326
PubChem CID:	21596158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21458	Radix paeoniae rubra	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	5

Activity Type	# Activity
Cell Line	4
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Survival	=	65.0	%	PMID[518774]
NPT65	Cell Line	HepG2	Homo sapiens	Survival	=	84.6	%	PMID[518774]
NPT65	Cell Line	HepG2	Homo sapiens	Survival	=	96.7	%	PMID[518774]
NPT65	Cell Line	HepG2	Homo sapiens	Survival	=	100.0	%	PMID[518774]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	1900.0	nM	PMID[518776]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	IC50	=	100.0	nM	PMID[518776]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	28800.0	nM	PMID[518775]
NPT35	Others	n.a.		IC50	>	500000.0	nM	PMID[518775]
NPT2	Others	Unspecified		Ratio IC50	=	30.0	n.a.	PMID[518776]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC130520 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1318
0.2-0.3	4830
0.3-0.4	14254
0.4-0.5	8958
0.5-0.6	5396
0.6-0.7	4786
0.7-0.8	2205
0.8-0.85	352
0.85-0.9	136
0.9-0.95	140
0.95-1	120

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263393
1.0	High Similarity	NPC234346
1.0	High Similarity	NPC225585
1.0	High Similarity	NPC293048
1.0	High Similarity	NPC121798
1.0	High Similarity	NPC270768
1.0	High Similarity	NPC61543
1.0	High Similarity	NPC59263
1.0	High Similarity	NPC127689
0.9881	High Similarity	NPC126369
0.9881	High Similarity	NPC470589
0.9881	High Similarity	NPC130278
0.9881	High Similarity	NPC111110
0.988	High Similarity	NPC52169
0.988	High Similarity	NPC182797
0.9765	High Similarity	NPC228784
0.9765	High Similarity	NPC155120
0.9765	High Similarity	NPC324341
0.9765	High Similarity	NPC282616
0.9765	High Similarity	NPC288833
0.9765	High Similarity	NPC966
0.9762	High Similarity	NPC274330
0.9762	High Similarity	NPC198664
0.9762	High Similarity	NPC143232
0.9762	High Similarity	NPC64872
0.9762	High Similarity	NPC290972
0.9762	High Similarity	NPC25906
0.9759	High Similarity	NPC98442
0.9759	High Similarity	NPC307426
0.9759	High Similarity	NPC293564
0.9759	High Similarity	NPC130577
0.9759	High Similarity	NPC51700
0.9759	High Similarity	NPC88716
0.9759	High Similarity	NPC68160
0.9759	High Similarity	NPC242468
0.9759	High Similarity	NPC142415
0.9759	High Similarity	NPC171203
0.9759	High Similarity	NPC102683
0.9759	High Similarity	NPC18064
0.9651	High Similarity	NPC229281
0.9651	High Similarity	NPC86368
0.9647	High Similarity	NPC210037
0.9647	High Similarity	NPC290614
0.9647	High Similarity	NPC291028
0.9647	High Similarity	NPC120968
0.9647	High Similarity	NPC86372
0.9647	High Similarity	NPC273621
0.9647	High Similarity	NPC18872
0.9647	High Similarity	NPC227467
0.9647	High Similarity	NPC172361
0.9647	High Similarity	NPC477872
0.9647	High Similarity	NPC7260
0.9643	High Similarity	NPC17733
0.9643	High Similarity	NPC290690
0.9643	High Similarity	NPC470629
0.9643	High Similarity	NPC246708
0.9643	High Similarity	NPC473242
0.9643	High Similarity	NPC40552
0.9643	High Similarity	NPC181225
0.9643	High Similarity	NPC474512
0.9639	High Similarity	NPC72638
0.954	High Similarity	NPC6818
0.954	High Similarity	NPC222047
0.954	High Similarity	NPC191412
0.954	High Similarity	NPC145667
0.954	High Similarity	NPC88116
0.954	High Similarity	NPC299996
0.954	High Similarity	NPC231063
0.954	High Similarity	NPC114159
0.954	High Similarity	NPC282395
0.954	High Similarity	NPC263548
0.954	High Similarity	NPC159365
0.954	High Similarity	NPC20235
0.954	High Similarity	NPC32407
0.9535	High Similarity	NPC187722
0.9535	High Similarity	NPC105189
0.9535	High Similarity	NPC65120
0.9535	High Similarity	NPC471588
0.9535	High Similarity	NPC158030
0.9535	High Similarity	NPC71074
0.9535	High Similarity	NPC306541
0.9535	High Similarity	NPC235884
0.9535	High Similarity	NPC84319
0.9535	High Similarity	NPC300351
0.9535	High Similarity	NPC4036
0.9535	High Similarity	NPC25299
0.9535	High Similarity	NPC52021
0.9535	High Similarity	NPC145067
0.9535	High Similarity	NPC6255
0.9535	High Similarity	NPC472149
0.9535	High Similarity	NPC233455
0.9535	High Similarity	NPC474525
0.9535	High Similarity	NPC475708
0.9529	High Similarity	NPC470588
0.9529	High Similarity	NPC474972
0.9529	High Similarity	NPC161751
0.9529	High Similarity	NPC95246
0.9432	High Similarity	NPC148523
0.9425	High Similarity	NPC214756
0.9425	High Similarity	NPC307335
0.9425	High Similarity	NPC298554
0.9425	High Similarity	NPC158059
0.9425	High Similarity	NPC202728
0.9425	High Similarity	NPC136313
0.9425	High Similarity	NPC295643
0.9425	High Similarity	NPC272075
0.9425	High Similarity	NPC118490
0.9425	High Similarity	NPC275809
0.9425	High Similarity	NPC118519
0.9425	High Similarity	NPC74855
0.9419	High Similarity	NPC474728
0.9419	High Similarity	NPC46441
0.9419	High Similarity	NPC193750
0.9419	High Similarity	NPC120840
0.9419	High Similarity	NPC113989
0.9419	High Similarity	NPC49320
0.9405	High Similarity	NPC213412
0.9326	High Similarity	NPC116457
0.9326	High Similarity	NPC476318
0.9326	High Similarity	NPC307282
0.9326	High Similarity	NPC204961
0.9326	High Similarity	NPC173744
0.9326	High Similarity	NPC25848
0.9326	High Similarity	NPC19376
0.9326	High Similarity	NPC305464
0.9326	High Similarity	NPC476327
0.9326	High Similarity	NPC73004
0.9326	High Similarity	NPC201657
0.9326	High Similarity	NPC98874
0.9326	High Similarity	NPC132824
0.9318	High Similarity	NPC474529
0.9318	High Similarity	NPC80365
0.9318	High Similarity	NPC91010
0.9318	High Similarity	NPC78580
0.9318	High Similarity	NPC209868
0.9318	High Similarity	NPC23621
0.9318	High Similarity	NPC184006
0.931	High Similarity	NPC38754
0.931	High Similarity	NPC77099
0.931	High Similarity	NPC60755
0.931	High Similarity	NPC470590
0.931	High Similarity	NPC285184
0.9302	High Similarity	NPC474686
0.9302	High Similarity	NPC30522
0.9294	High Similarity	NPC71507
0.9286	High Similarity	NPC133954
0.9222	High Similarity	NPC476878
0.9222	High Similarity	NPC247139
0.9222	High Similarity	NPC9613
0.9222	High Similarity	NPC106112
0.9222	High Similarity	NPC261935
0.9222	High Similarity	NPC476879
0.9213	High Similarity	NPC96916
0.9213	High Similarity	NPC473240
0.9213	High Similarity	NPC474727
0.9213	High Similarity	NPC139570
0.9213	High Similarity	NPC83693
0.9213	High Similarity	NPC32118
0.9213	High Similarity	NPC195715
0.9213	High Similarity	NPC23241
0.9213	High Similarity	NPC198245
0.9205	High Similarity	NPC474436
0.9205	High Similarity	NPC63118
0.9205	High Similarity	NPC474806
0.9205	High Similarity	NPC49776
0.9205	High Similarity	NPC133579
0.9176	High Similarity	NPC95594
0.9176	High Similarity	NPC73038
0.9176	High Similarity	NPC475862
0.9176	High Similarity	NPC74363
0.9176	High Similarity	NPC477579
0.9176	High Similarity	NPC235341
0.9167	High Similarity	NPC171789
0.9121	High Similarity	NPC174663
0.9121	High Similarity	NPC111214
0.9121	High Similarity	NPC271614
0.9121	High Similarity	NPC164349
0.9121	High Similarity	NPC29765
0.9111	High Similarity	NPC157113
0.9111	High Similarity	NPC207922
0.9111	High Similarity	NPC62516
0.9111	High Similarity	NPC259733
0.9111	High Similarity	NPC327179
0.9111	High Similarity	NPC158371
0.9111	High Similarity	NPC230151
0.9101	High Similarity	NPC60692
0.9101	High Similarity	NPC87095
0.9101	High Similarity	NPC188102
0.9101	High Similarity	NPC296164
0.9101	High Similarity	NPC74751
0.9091	High Similarity	NPC301244
0.908	High Similarity	NPC281524
0.908	High Similarity	NPC475921
0.908	High Similarity	NPC474704
0.907	High Similarity	NPC46912
0.907	High Similarity	NPC158141
0.907	High Similarity	NPC173089
0.907	High Similarity	NPC73064
0.907	High Similarity	NPC162107
0.9022	High Similarity	NPC35239

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC130520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1662
0.2-0.3	3841
0.3-0.4	2312
0.4-0.5	688
0.5-0.6	208
0.6-0.7	171
0.7-0.8	80
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9535	High Similarity	NPD7515	Phase 2
0.9101	High Similarity	NPD7748	Approved
0.8804	High Similarity	NPD7902	Approved
0.8621	High Similarity	NPD7520	Clinical (unspecified phase)
0.8571	High Similarity	NPD7645	Phase 2
0.8478	Intermediate Similarity	NPD7900	Approved
0.8478	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD3618	Phase 1
0.809	Intermediate Similarity	NPD4786	Approved
0.8068	Intermediate Similarity	NPD3667	Approved
0.8065	Intermediate Similarity	NPD8034	Phase 2
0.8065	Intermediate Similarity	NPD8035	Phase 2
0.8043	Intermediate Similarity	NPD5328	Approved
0.7979	Intermediate Similarity	NPD6399	Phase 3
0.7872	Intermediate Similarity	NPD6079	Approved
0.7849	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD6675	Approved
0.7822	Intermediate Similarity	NPD6402	Approved
0.7822	Intermediate Similarity	NPD7128	Approved
0.7822	Intermediate Similarity	NPD5739	Approved
0.7755	Intermediate Similarity	NPD7638	Approved
0.7742	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3666	Approved
0.7692	Intermediate Similarity	NPD3665	Phase 1
0.7692	Intermediate Similarity	NPD3133	Approved
0.7684	Intermediate Similarity	NPD6411	Approved
0.7677	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7639	Approved
0.767	Intermediate Similarity	NPD6881	Approved
0.767	Intermediate Similarity	NPD6899	Approved
0.767	Intermediate Similarity	NPD7320	Approved
0.7653	Intermediate Similarity	NPD4755	Approved
0.7653	Intermediate Similarity	NPD6083	Phase 2
0.7653	Intermediate Similarity	NPD6084	Phase 2
0.764	Intermediate Similarity	NPD7525	Registered
0.7604	Intermediate Similarity	NPD4202	Approved
0.7596	Intermediate Similarity	NPD6372	Approved
0.7596	Intermediate Similarity	NPD6373	Approved
0.7586	Intermediate Similarity	NPD6117	Approved
0.7573	Intermediate Similarity	NPD5701	Approved
0.7573	Intermediate Similarity	NPD5697	Approved
0.7551	Intermediate Similarity	NPD5222	Approved
0.7551	Intermediate Similarity	NPD4697	Phase 3
0.7551	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5221	Approved
0.7527	Intermediate Similarity	NPD6684	Approved
0.7527	Intermediate Similarity	NPD7334	Approved
0.7527	Intermediate Similarity	NPD5330	Approved
0.7527	Intermediate Similarity	NPD7521	Approved
0.7527	Intermediate Similarity	NPD6409	Approved
0.7527	Intermediate Similarity	NPD7146	Approved
0.7524	Intermediate Similarity	NPD7102	Approved
0.7524	Intermediate Similarity	NPD7290	Approved
0.7524	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.7475	Intermediate Similarity	NPD5173	Approved
0.7474	Intermediate Similarity	NPD6101	Approved
0.7474	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4753	Phase 2
0.7453	Intermediate Similarity	NPD8130	Phase 1
0.7453	Intermediate Similarity	NPD6617	Approved
0.7453	Intermediate Similarity	NPD6650	Approved
0.7453	Intermediate Similarity	NPD6869	Approved
0.7453	Intermediate Similarity	NPD6649	Approved
0.7453	Intermediate Similarity	NPD6847	Approved
0.7447	Intermediate Similarity	NPD3573	Approved
0.7429	Intermediate Similarity	NPD6012	Approved
0.7429	Intermediate Similarity	NPD6014	Approved
0.7429	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6013	Approved
0.7416	Intermediate Similarity	NPD6114	Approved
0.7416	Intermediate Similarity	NPD6697	Approved
0.7416	Intermediate Similarity	NPD6115	Approved
0.7416	Intermediate Similarity	NPD6118	Approved
0.7383	Intermediate Similarity	NPD6882	Approved
0.7383	Intermediate Similarity	NPD8297	Approved
0.7374	Intermediate Similarity	NPD7614	Phase 1
0.7368	Intermediate Similarity	NPD6903	Approved
0.7368	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD5737	Approved
0.7356	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5224	Approved
0.7353	Intermediate Similarity	NPD5211	Phase 2
0.7353	Intermediate Similarity	NPD5226	Approved
0.7353	Intermediate Similarity	NPD5225	Approved
0.7353	Intermediate Similarity	NPD4633	Approved
0.7345	Intermediate Similarity	NPD8328	Phase 3
0.7333	Intermediate Similarity	NPD6011	Approved
0.729	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5175	Approved
0.7282	Intermediate Similarity	NPD5174	Approved
0.7273	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7339	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD6942	Approved
0.7255	Intermediate Similarity	NPD5223	Approved
0.7253	Intermediate Similarity	NPD4695	Discontinued
0.7228	Intermediate Similarity	NPD5696	Approved
0.7212	Intermediate Similarity	NPD5141	Approved
0.7191	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD4768	Approved
0.7115	Intermediate Similarity	NPD4754	Approved
0.71	Intermediate Similarity	NPD4629	Approved
0.71	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5210	Approved
0.7097	Intermediate Similarity	NPD4221	Approved
0.7097	Intermediate Similarity	NPD4223	Phase 3
0.7075	Intermediate Similarity	NPD6412	Phase 2
0.7071	Intermediate Similarity	NPD5778	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD4225	Approved
0.7053	Intermediate Similarity	NPD5329	Approved
0.703	Intermediate Similarity	NPD7732	Phase 3
0.7027	Intermediate Similarity	NPD6274	Approved
0.7027	Intermediate Similarity	NPD6868	Approved
0.7021	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD4729	Approved
0.7009	Intermediate Similarity	NPD4730	Approved
0.7009	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.6991	Remote Similarity	NPD7100	Approved
0.6991	Remote Similarity	NPD7101	Approved
0.6979	Remote Similarity	NPD6098	Approved
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6947	Remote Similarity	NPD4197	Approved
0.6944	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6673	Approved
0.6939	Remote Similarity	NPD6904	Approved
0.6939	Remote Similarity	NPD6080	Approved
0.6932	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6335	Approved
0.6897	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4634	Approved
0.6881	Remote Similarity	NPD5249	Phase 3
0.6881	Remote Similarity	NPD5247	Approved
0.6881	Remote Similarity	NPD5248	Approved
0.6881	Remote Similarity	NPD5250	Approved
0.6881	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD6909	Approved
0.687	Remote Similarity	NPD6908	Approved
0.6852	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD5168	Approved
0.6848	Remote Similarity	NPD3617	Approved
0.6848	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8133	Approved
0.6822	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD5215	Approved
0.6818	Remote Similarity	NPD5217	Approved
0.6818	Remote Similarity	NPD5216	Approved
0.6814	Remote Similarity	NPD6009	Approved
0.6814	Remote Similarity	NPD6317	Approved
0.6807	Remote Similarity	NPD7736	Approved
0.6804	Remote Similarity	NPD4138	Approved
0.6804	Remote Similarity	NPD5205	Approved
0.6804	Remote Similarity	NPD4688	Approved
0.6804	Remote Similarity	NPD4689	Approved
0.6804	Remote Similarity	NPD4623	Approved
0.6804	Remote Similarity	NPD4519	Discontinued
0.6804	Remote Similarity	NPD4690	Approved
0.6804	Remote Similarity	NPD4693	Phase 3
0.6783	Remote Similarity	NPD6319	Approved
0.678	Remote Similarity	NPD7507	Approved
0.6754	Remote Similarity	NPD6314	Approved
0.6754	Remote Similarity	NPD6313	Approved
0.6727	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5135	Approved
0.6727	Remote Similarity	NPD5169	Approved
0.6703	Remote Similarity	NPD3703	Phase 2
0.6702	Remote Similarity	NPD5368	Approved
0.6702	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1694	Approved
0.6697	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6639	Remote Similarity	NPD6616	Approved
0.6638	Remote Similarity	NPD6059	Approved
0.6638	Remote Similarity	NPD6054	Approved
0.6634	Remote Similarity	NPD7637	Suspended
0.6634	Remote Similarity	NPD5693	Phase 1
0.6634	Remote Similarity	NPD6050	Approved
0.6633	Remote Similarity	NPD5280	Approved
0.6633	Remote Similarity	NPD5690	Phase 2
0.6633	Remote Similarity	NPD4694	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data