NPASS Compound

Structure

CID274330 OpenBabel06191716082D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3496 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8625 1.1049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 2.9231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 3.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 8 22 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 2 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 6 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 6 0 0 0 24 29 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 5 1 6 0 0 0 28 30 1 1 0 0 0 29 25 1 6 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	4.883
LogD:	4.55
LogS:	-4.178
# 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:	0.427
Synthetic Accessibility Score:	4.912
Fsp3:	0.9
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:	-5.393
MDCK Permeability:	9.579887773725204e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.289
30% Bioavailability (F30%):	0.529

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	97.14278411865234%
Volume Distribution (VD):	0.629
Pgp-substrate:	1.8094433546066284%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.258
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.342
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	3.655
Half-life (T1/2):	0.225

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.437
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.039
Carcinogencity:	0.035
Eye Corrosion:	0.273
Eye Irritation:	0.215
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC274330

Natural Product ID:	NPC274330
*Common Name:**	3Beta,27-Dihydroxy-12-Ursen-28-Oic Acid
IUPAC Name:	(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-(hydroxymethyl)-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	YBQHMGFOAOJZCG-PDGODTHUSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18-9-14-29(25(33)34)15-16-30(17-31)20(24(29)19(18)2)7-8-22-27(5)12-11-23(32)26(3,4)21(27)10-13-28(22,30)6/h7,18-19,21-24,31-32H,8-17H2,1-6H3,(H,33,34)/t18-,19+,21+,22-,23+,24+,27+,28-,29+,30+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(CO)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@H]1C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524080
PubChem CID:	44583858
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	144000.0	nM	PMID[494615]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	236000.0	nM	PMID[494615]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	67100.0	nM	PMID[494615]
NPT27	Others	Unspecified		IC50	=	7200.0	nM	PMID[494615]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	99700.0	nM	PMID[494615]

☑ 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 NPC274330 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	203
0.1-0.2	1265
0.2-0.3	4724
0.3-0.4	14189
0.4-0.5	9054
0.5-0.6	5587
0.6-0.7	4797
0.7-0.8	2242
0.8-0.85	236
0.85-0.9	144
0.9-0.95	142
0.95-1	114

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC198664
1.0	High Similarity	NPC143232
0.9881	High Similarity	NPC126369
0.9881	High Similarity	NPC470589
0.9881	High Similarity	NPC111110
0.988	High Similarity	NPC52169
0.988	High Similarity	NPC182797
0.988	High Similarity	NPC290690
0.988	High Similarity	NPC470629
0.988	High Similarity	NPC181225
0.988	High Similarity	NPC17733
0.988	High Similarity	NPC474512
0.988	High Similarity	NPC473242
0.9765	High Similarity	NPC187722
0.9762	High Similarity	NPC270768
0.9762	High Similarity	NPC59263
0.9762	High Similarity	NPC130520
0.9762	High Similarity	NPC121798
0.9762	High Similarity	NPC127689
0.9762	High Similarity	NPC234346
0.9762	High Similarity	NPC263393
0.9762	High Similarity	NPC61543
0.9762	High Similarity	NPC470588
0.9762	High Similarity	NPC225585
0.9762	High Similarity	NPC293048
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	NPC88716
0.9759	High Similarity	NPC68160
0.9759	High Similarity	NPC242468
0.9759	High Similarity	NPC51700
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	NPC158059
0.9651	High Similarity	NPC202728
0.9651	High Similarity	NPC118519
0.9647	High Similarity	NPC210037
0.9647	High Similarity	NPC290614
0.9647	High Similarity	NPC291028
0.9647	High Similarity	NPC130278
0.9647	High Similarity	NPC120968
0.9647	High Similarity	NPC273621
0.9647	High Similarity	NPC474728
0.9647	High Similarity	NPC18872
0.9647	High Similarity	NPC227467
0.9647	High Similarity	NPC477872
0.9647	High Similarity	NPC7260
0.9643	High Similarity	NPC246708
0.9643	High Similarity	NPC40552
0.9639	High Similarity	NPC72638
0.954	High Similarity	NPC6818
0.954	High Similarity	NPC191412
0.954	High Similarity	NPC114159
0.954	High Similarity	NPC159365
0.954	High Similarity	NPC209868
0.9535	High Similarity	NPC235884
0.9535	High Similarity	NPC38754
0.9535	High Similarity	NPC105189
0.9535	High Similarity	NPC228784
0.9535	High Similarity	NPC65120
0.9535	High Similarity	NPC158030
0.9535	High Similarity	NPC71074
0.9535	High Similarity	NPC288833
0.9535	High Similarity	NPC84319
0.9535	High Similarity	NPC155120
0.9535	High Similarity	NPC282616
0.9535	High Similarity	NPC300351
0.9535	High Similarity	NPC77099
0.9535	High Similarity	NPC25299
0.9535	High Similarity	NPC52021
0.9535	High Similarity	NPC285184
0.9535	High Similarity	NPC145067
0.9535	High Similarity	NPC472149
0.9535	High Similarity	NPC233455
0.9535	High Similarity	NPC324341
0.9535	High Similarity	NPC4036
0.9535	High Similarity	NPC306541
0.9535	High Similarity	NPC60755
0.9535	High Similarity	NPC474525
0.9535	High Similarity	NPC966
0.9535	High Similarity	NPC470590
0.9529	High Similarity	NPC474686
0.9529	High Similarity	NPC474972
0.9529	High Similarity	NPC161751
0.9529	High Similarity	NPC95246
0.9524	High Similarity	NPC71507
0.9432	High Similarity	NPC473240
0.9432	High Similarity	NPC96916
0.9425	High Similarity	NPC214756
0.9425	High Similarity	NPC133579
0.9425	High Similarity	NPC86368
0.9425	High Similarity	NPC307335
0.9425	High Similarity	NPC298554
0.9425	High Similarity	NPC474806
0.9425	High Similarity	NPC136313
0.9425	High Similarity	NPC295643
0.9425	High Similarity	NPC275809
0.9425	High Similarity	NPC74855
0.9425	High Similarity	NPC272075
0.9419	High Similarity	NPC46441
0.9419	High Similarity	NPC120840
0.9419	High Similarity	NPC113989
0.9419	High Similarity	NPC86372
0.9419	High Similarity	NPC193750
0.9419	High Similarity	NPC172361
0.9419	High Similarity	NPC49320
0.9326	High Similarity	NPC116457
0.9326	High Similarity	NPC476318
0.9326	High Similarity	NPC204961
0.9326	High Similarity	NPC476327
0.9326	High Similarity	NPC173744
0.9326	High Similarity	NPC207922
0.9326	High Similarity	NPC259733
0.9326	High Similarity	NPC327179
0.9326	High Similarity	NPC158371
0.9326	High Similarity	NPC73004
0.9326	High Similarity	NPC157113
0.9326	High Similarity	NPC62516
0.9326	High Similarity	NPC132824
0.9318	High Similarity	NPC263548
0.9318	High Similarity	NPC299996
0.9318	High Similarity	NPC282395
0.9318	High Similarity	NPC32407
0.9318	High Similarity	NPC474529
0.9318	High Similarity	NPC145667
0.9318	High Similarity	NPC91010
0.9318	High Similarity	NPC20235
0.9318	High Similarity	NPC80365
0.9318	High Similarity	NPC222047
0.9318	High Similarity	NPC88116
0.9318	High Similarity	NPC87095
0.9318	High Similarity	NPC231063
0.931	High Similarity	NPC471588
0.931	High Similarity	NPC475708
0.931	High Similarity	NPC6255
0.931	High Similarity	NPC301244
0.9302	High Similarity	NPC30522
0.9294	High Similarity	NPC73064
0.9286	High Similarity	NPC133954
0.9222	High Similarity	NPC247139
0.9222	High Similarity	NPC9613
0.9222	High Similarity	NPC189880
0.9222	High Similarity	NPC187933
0.9222	High Similarity	NPC259788
0.9222	High Similarity	NPC255589
0.9222	High Similarity	NPC43686
0.9213	High Similarity	NPC474727
0.9213	High Similarity	NPC32118
0.9213	High Similarity	NPC139570
0.9213	High Similarity	NPC195715
0.9213	High Similarity	NPC148523
0.9213	High Similarity	NPC198245
0.9205	High Similarity	NPC474436
0.9205	High Similarity	NPC63118
0.9205	High Similarity	NPC118490
0.9205	High Similarity	NPC49776
0.9186	High Similarity	NPC474511
0.9186	High Similarity	NPC1753
0.9176	High Similarity	NPC95594
0.9176	High Similarity	NPC73038
0.9176	High Similarity	NPC475862
0.9176	High Similarity	NPC213412
0.9176	High Similarity	NPC56588
0.9176	High Similarity	NPC74363
0.9176	High Similarity	NPC477579
0.9176	High Similarity	NPC235341
0.9167	High Similarity	NPC180834
0.9167	High Similarity	NPC171789
0.9121	High Similarity	NPC174663
0.9121	High Similarity	NPC260149
0.9121	High Similarity	NPC271614
0.9121	High Similarity	NPC111214
0.9121	High Similarity	NPC58942
0.9121	High Similarity	NPC29765
0.9111	High Similarity	NPC25848
0.9111	High Similarity	NPC19376
0.9111	High Similarity	NPC98874
0.9111	High Similarity	NPC201657
0.9111	High Similarity	NPC307282
0.9111	High Similarity	NPC230151
0.9111	High Similarity	NPC305464
0.9101	High Similarity	NPC78580
0.9101	High Similarity	NPC60692
0.9101	High Similarity	NPC23621
0.9101	High Similarity	NPC188102
0.9101	High Similarity	NPC148964
0.9101	High Similarity	NPC296164
0.9101	High Similarity	NPC74751
0.9101	High Similarity	NPC184006
0.908	High Similarity	NPC281524
0.907	High Similarity	NPC46912
0.907	High Similarity	NPC158141

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 NPC274330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1613
0.2-0.3	3799
0.3-0.4	2364
0.4-0.5	718
0.5-0.6	215
0.6-0.7	191
0.7-0.8	61
0.8-0.85	3
0.85-0.9	2
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)
0.8478	Intermediate Similarity	NPD7900	Approved
0.8478	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7645	Phase 2
0.8295	Intermediate Similarity	NPD4786	Approved
0.8276	Intermediate Similarity	NPD3667	Approved
0.8172	Intermediate Similarity	NPD6399	Phase 3
0.8111	Intermediate Similarity	NPD3618	Phase 1
0.8065	Intermediate Similarity	NPD8034	Phase 2
0.8065	Intermediate Similarity	NPD8035	Phase 2
0.8043	Intermediate Similarity	NPD5328	Approved
0.8043	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6079	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	NPD3668	Phase 3
0.7692	Intermediate Similarity	NPD3133	Approved
0.7684	Intermediate Similarity	NPD6411	Approved
0.7677	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7639	Approved
0.7647	Intermediate Similarity	NPD6675	Approved
0.7647	Intermediate Similarity	NPD5739	Approved
0.7647	Intermediate Similarity	NPD6402	Approved
0.7647	Intermediate Similarity	NPD7128	Approved
0.764	Intermediate Similarity	NPD7525	Registered
0.7604	Intermediate Similarity	NPD4202	Approved
0.7586	Intermediate Similarity	NPD6117	Approved
0.7551	Intermediate Similarity	NPD4697	Phase 3
0.7551	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5221	Approved
0.7551	Intermediate Similarity	NPD5222	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
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.7475	Intermediate Similarity	NPD4755	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD5173	Approved
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7474	Intermediate Similarity	NPD6101	Approved
0.7474	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6942	Approved
0.7471	Intermediate Similarity	NPD7339	Approved
0.7447	Intermediate Similarity	NPD3573	Approved
0.7444	Intermediate Similarity	NPD4695	Discontinued
0.7429	Intermediate Similarity	NPD6372	Approved
0.7429	Intermediate Similarity	NPD6373	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
0.7404	Intermediate Similarity	NPD5701	Approved
0.7404	Intermediate Similarity	NPD5697	Approved
0.7386	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
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
0.7358	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD7102	Approved
0.7358	Intermediate Similarity	NPD7290	Approved
0.7356	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6011	Approved
0.7327	Intermediate Similarity	NPD5285	Approved
0.7327	Intermediate Similarity	NPD5286	Approved
0.7327	Intermediate Similarity	NPD4700	Approved
0.7327	Intermediate Similarity	NPD4696	Approved
0.7292	Intermediate Similarity	NPD4753	Phase 2
0.729	Intermediate Similarity	NPD6869	Approved
0.729	Intermediate Similarity	NPD6847	Approved
0.729	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6650	Approved
0.729	Intermediate Similarity	NPD6617	Approved
0.729	Intermediate Similarity	NPD6649	Approved
0.729	Intermediate Similarity	NPD8130	Phase 1
0.7273	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7264	Intermediate Similarity	NPD6012	Approved
0.7264	Intermediate Similarity	NPD6014	Approved
0.7264	Intermediate Similarity	NPD6013	Approved
0.7264	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5223	Approved
0.7222	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6882	Approved
0.7193	Intermediate Similarity	NPD8328	Phase 3
0.7184	Intermediate Similarity	NPD5226	Approved
0.7184	Intermediate Similarity	NPD4633	Approved
0.7184	Intermediate Similarity	NPD5211	Phase 2
0.7184	Intermediate Similarity	NPD5225	Approved
0.7184	Intermediate Similarity	NPD5224	Approved
0.7158	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5279	Phase 3
0.7115	Intermediate Similarity	NPD5174	Approved
0.7115	Intermediate Similarity	NPD5175	Approved
0.7115	Intermediate Similarity	NPD4754	Approved
0.71	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5695	Phase 3
0.7097	Intermediate Similarity	NPD4221	Approved
0.7097	Intermediate Similarity	NPD4223	Phase 3
0.7071	Intermediate Similarity	NPD5778	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD5696	Approved
0.7053	Intermediate Similarity	NPD5329	Approved
0.7048	Intermediate Similarity	NPD5141	Approved
0.703	Intermediate Similarity	NPD7732	Phase 3
0.7027	Intermediate Similarity	NPD6868	Approved
0.7021	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD4632	Approved
0.6981	Remote Similarity	NPD4767	Approved
0.6981	Remote Similarity	NPD6008	Approved
0.6981	Remote Similarity	NPD4768	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
0.6939	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)
0.6931	Remote Similarity	NPD4629	Approved
0.6931	Remote Similarity	NPD5210	Approved
0.6916	Remote Similarity	NPD6412	Phase 2
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)
0.6882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6274	Approved
0.6852	Remote Similarity	NPD4730	Approved
0.6852	Remote Similarity	NPD5128	Approved
0.6852	Remote Similarity	NPD5168	Approved
0.6852	Remote Similarity	NPD4729	Approved
0.6848	Remote Similarity	NPD3617	Approved
0.6848	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7100	Approved
0.6842	Remote Similarity	NPD7101	Approved
0.6814	Remote Similarity	NPD6317	Approved
0.6814	Remote Similarity	NPD6009	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
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6926	Approved
0.6778	Remote Similarity	NPD6924	Approved
0.6754	Remote Similarity	NPD6314	Approved
0.6754	Remote Similarity	NPD6313	Approved
0.6727	Remote Similarity	NPD5249	Phase 3
0.6727	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5247	Approved
0.6727	Remote Similarity	NPD5135	Approved
0.6727	Remote Similarity	NPD5251	Approved
0.6727	Remote Similarity	NPD5250	Approved
0.6727	Remote Similarity	NPD5169	Approved
0.6727	Remote Similarity	NPD5248	Approved
0.6727	Remote Similarity	NPD4634	Approved
0.6724	Remote Similarity	NPD6909	Approved
0.6724	Remote Similarity	NPD6908	Approved
0.6703	Remote Similarity	NPD3703	Phase 2
0.6703	Remote Similarity	NPD8264	Approved
0.6701	Remote Similarity	NPD1694	Approved
0.6697	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD6319	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
0.6632	Remote Similarity	NPD5369	Approved
0.663	Remote Similarity	NPD6933	Approved
0.6629	Remote Similarity	NPD4245	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