NPASS Compound

Structure

CID261935 OpenBabel06191716062D 36 40 0 0 1 0 0 0 0 0999 V2000 4.4770 0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9985 -1.0817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0225 0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 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 -2.5347 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9981 0.6185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -0.2264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 4 27 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 28 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 30 1 0 0 0 0 15 18 1 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 6 0 0 0 19 22 1 0 0 0 0 19 31 1 1 0 0 0 20 26 1 1 0 0 0 20 28 1 0 0 0 0 21 26 1 1 0 0 0 21 29 1 0 0 0 0 22 29 1 1 0 0 0 22 32 1 0 0 0 0 23 29 1 0 0 0 0 23 33 2 0 0 0 0 23 34 1 0 0 0 0 24 35 2 0 0 0 0 24 36 1 0 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 6 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.33
Volume:	529.486
LogP:	4.376
LogD:	3.626
LogS:	-3.403
# Rotatable Bonds:	2
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	4.943
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.871
MDCK Permeability:	1.0036915227829013e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.638

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.48
Plasma Protein Binding (PPB):	90.17405700683594%
Volume Distribution (VD):	0.485
Pgp-substrate:	9.515141487121582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.592
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.725
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.505
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.148
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	1.292
Half-life (T1/2):	0.339

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.498
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.591
Skin Sensitization:	0.041
Carcinogencity:	0.241
Eye Corrosion:	0.061
Eye Irritation:	0.042
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC261935

Natural Product ID:	NPC261935
*Common Name:**	(2S,3R,4S,4Ar,6Ar,6Bs,8As,12As,14Ar,14Br)-2,3-Dihydroxy-4,6A,6B,11,11,14B-Hexamethyl-1,2,3,4A,5,6,7,8,9,10,12,12A,14,14A-Tetradecahydropicene-4,8A-Dicarboxylic Acid
IUPAC Name:	(2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
Synonyms:	NSC-382025
Standard InCHIKey:	IDGXIXSKISLYAC-WNTKNEGGSA-N
Standard InCHI:	InChI=1S/C30H46O6/c1-25(2)11-13-30(24(35)36)14-12-27(4)17(18(30)15-25)7-8-20-26(3)16-19(31)22(32)29(6,23(33)34)21(26)9-10-28(20,27)5/h7,18-22,31-32H,8-16H2,1-6H3,(H,33,34)(H,35,36)/t18-,19-,20+,21+,22-,26+,27+,28+,29-,30-/m0/s1
SMILES:	O[C@H]1C[C@@]2(C)[C@H]([C@]([C@H]1O)(C)C(=O)O)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520726
PubChem CID:	65048
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
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14703354]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800643]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	Brazil	n.a.	PMID[18177008]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO10350	Erythrina speciosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17806	Richteria pyrethroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25832	Helichrysum drakensbergense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26847	Lecidea quernea	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26151	Santolina pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25797	Piper divaricatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27103	Satureja vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27030	Commiphora sphaerocarpa	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10677	Prunus prostrata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26218	Prosopis africana	Species	Fabaceae	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
GI50	60
IC50	2
Others	7

Activity Type	# Activity
Cell Line	63
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	31622.78	nM	PMID[463261]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	78342.96	nM	PMID[463261]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	79067.86	nM	PMID[463261]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	86896.04	nM	PMID[463261]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	82224.26	nM	PMID[463261]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	54575.79	nM	PMID[463261]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	89330.55	nM	PMID[463261]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	90782.05	nM	PMID[463261]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[463261]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	30400.0	nM	PMID[463262]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	40.7	%	PMID[463262]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Activity	=	100.0	%	PMID[463262]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Activity	=	100.0	%	PMID[463262]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	40000.0	nM	PMID[463262]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Activity	=	71.7	%	PMID[463262]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	60.14	%	PMID[463263]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	61.12	%	PMID[463263]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	62.16	%	PMID[463263]

☑ 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 NPC261935 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	226
0.1-0.2	1423
0.2-0.3	4774
0.3-0.4	11999
0.4-0.5	10917
0.5-0.6	5771
0.6-0.7	4798
0.7-0.8	2013
0.8-0.85	488
0.85-0.9	116
0.9-0.95	148
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106112
0.989	High Similarity	NPC111214
0.989	High Similarity	NPC271614
0.989	High Similarity	NPC29765
0.9889	High Similarity	NPC201657
0.9783	High Similarity	NPC35239
0.967	High Similarity	NPC204961
0.967	High Similarity	NPC73004
0.967	High Similarity	NPC173744
0.9667	High Similarity	NPC263548
0.9667	High Similarity	NPC20235
0.9667	High Similarity	NPC145667
0.9667	High Similarity	NPC299996
0.9667	High Similarity	NPC282395
0.9667	High Similarity	NPC231063
0.9667	High Similarity	NPC32407
0.9667	High Similarity	NPC88116
0.9565	High Similarity	NPC9613
0.9565	High Similarity	NPC247139
0.956	High Similarity	NPC96916
0.9462	High Similarity	NPC188833
0.9457	High Similarity	NPC25848
0.9457	High Similarity	NPC132824
0.9457	High Similarity	NPC19376
0.9457	High Similarity	NPC307282
0.9457	High Similarity	NPC305464
0.9457	High Similarity	NPC158371
0.9457	High Similarity	NPC259733
0.9457	High Similarity	NPC207922
0.9444	High Similarity	NPC84319
0.9444	High Similarity	NPC288833
0.9444	High Similarity	NPC306541
0.9444	High Similarity	NPC25299
0.9444	High Similarity	NPC472149
0.9444	High Similarity	NPC235884
0.9444	High Similarity	NPC324341
0.9444	High Similarity	NPC300351
0.9444	High Similarity	NPC282616
0.9444	High Similarity	NPC966
0.9444	High Similarity	NPC155120
0.9444	High Similarity	NPC52021
0.9444	High Similarity	NPC71074
0.9444	High Similarity	NPC228784
0.9355	High Similarity	NPC259788
0.9355	High Similarity	NPC43686
0.9355	High Similarity	NPC255589
0.9348	High Similarity	NPC32118
0.9341	High Similarity	NPC229281
0.9341	High Similarity	NPC136313
0.9341	High Similarity	NPC307335
0.9341	High Similarity	NPC275809
0.9341	High Similarity	NPC74855
0.9333	High Similarity	NPC49320
0.9333	High Similarity	NPC86372
0.9333	High Similarity	NPC477872
0.9333	High Similarity	NPC172361
0.9333	High Similarity	NPC290614
0.9333	High Similarity	NPC7260
0.9333	High Similarity	NPC18872
0.9333	High Similarity	NPC273621
0.9333	High Similarity	NPC120968
0.9333	High Similarity	NPC130278
0.9333	High Similarity	NPC227467
0.9333	High Similarity	NPC210037
0.9263	High Similarity	NPC256247
0.9255	High Similarity	NPC164349
0.9255	High Similarity	NPC174663
0.9239	High Similarity	NPC6818
0.9239	High Similarity	NPC191412
0.9239	High Similarity	NPC114159
0.9239	High Similarity	NPC222047
0.9231	High Similarity	NPC105189
0.9231	High Similarity	NPC6255
0.9231	High Similarity	NPC187722
0.9231	High Similarity	NPC471588
0.9222	High Similarity	NPC25906
0.9222	High Similarity	NPC290972
0.9222	High Similarity	NPC293048
0.9222	High Similarity	NPC127689
0.9222	High Similarity	NPC263393
0.9222	High Similarity	NPC64872
0.9222	High Similarity	NPC130520
0.9222	High Similarity	NPC121798
0.9222	High Similarity	NPC61543
0.9222	High Similarity	NPC270768
0.9222	High Similarity	NPC225585
0.9222	High Similarity	NPC59263
0.9222	High Similarity	NPC234346
0.9175	High Similarity	NPC284865
0.9149	High Similarity	NPC203343
0.9149	High Similarity	NPC187933
0.9149	High Similarity	NPC312075
0.914	High Similarity	NPC198245
0.914	High Similarity	NPC148523
0.913	High Similarity	NPC118519
0.913	High Similarity	NPC202728
0.913	High Similarity	NPC474806
0.913	High Similarity	NPC133579
0.913	High Similarity	NPC158059
0.913	High Similarity	NPC118490
0.913	High Similarity	NPC298554
0.9121	High Similarity	NPC111110
0.9121	High Similarity	NPC291028
0.9121	High Similarity	NPC470589
0.9121	High Similarity	NPC126369
0.9121	High Similarity	NPC193750
0.9111	High Similarity	NPC52169
0.9111	High Similarity	NPC182797
0.9062	High Similarity	NPC233012
0.9062	High Similarity	NPC54909
0.9043	High Similarity	NPC230151
0.9043	High Similarity	NPC98874
0.9043	High Similarity	NPC116457
0.9043	High Similarity	NPC88847
0.9032	High Similarity	NPC23621
0.9032	High Similarity	NPC148964
0.9032	High Similarity	NPC184006
0.9032	High Similarity	NPC188102
0.9032	High Similarity	NPC209868
0.9032	High Similarity	NPC474529
0.9032	High Similarity	NPC87095
0.9032	High Similarity	NPC78580
0.9022	High Similarity	NPC38754
0.9011	High Similarity	NPC143232
0.9011	High Similarity	NPC274330
0.9011	High Similarity	NPC198664
0.9	High Similarity	NPC171203
0.9	High Similarity	NPC130577
0.9	High Similarity	NPC293564
0.9	High Similarity	NPC307426
0.9	High Similarity	NPC142415
0.9	High Similarity	NPC98442
0.9	High Similarity	NPC102683
0.9	High Similarity	NPC18064
0.9	High Similarity	NPC242468
0.9	High Similarity	NPC51700
0.9	High Similarity	NPC88716
0.9	High Similarity	NPC68160
0.8936	High Similarity	NPC23241
0.8936	High Similarity	NPC83693
0.8936	High Similarity	NPC195715
0.8925	High Similarity	NPC86368
0.8901	High Similarity	NPC290690
0.8901	High Similarity	NPC17733
0.8901	High Similarity	NPC40552
0.8901	High Similarity	NPC181225
0.8901	High Similarity	NPC473242
0.8901	High Similarity	NPC246708
0.8901	High Similarity	NPC470629
0.8901	High Similarity	NPC474512
0.8889	High Similarity	NPC72638
0.8889	High Similarity	NPC80566
0.8842	High Similarity	NPC472806
0.8842	High Similarity	NPC157113
0.8842	High Similarity	NPC327179
0.8842	High Similarity	NPC167193
0.8842	High Similarity	NPC476327
0.8842	High Similarity	NPC476318
0.8842	High Similarity	NPC62516
0.883	High Similarity	NPC159365
0.883	High Similarity	NPC296164
0.883	High Similarity	NPC60692
0.8817	High Similarity	NPC475708
0.8817	High Similarity	NPC233455
0.8817	High Similarity	NPC4036
0.8817	High Similarity	NPC474525
0.8817	High Similarity	NPC145067
0.8817	High Similarity	NPC65120
0.8817	High Similarity	NPC158030
0.8804	High Similarity	NPC474972
0.8804	High Similarity	NPC161751
0.8804	High Similarity	NPC470588
0.8804	High Similarity	NPC95246
0.8791	High Similarity	NPC173089
0.8791	High Similarity	NPC477926
0.8791	High Similarity	NPC158141
0.8788	High Similarity	NPC475036
0.875	High Similarity	NPC26413
0.875	High Similarity	NPC89225
0.8737	High Similarity	NPC53565
0.8737	High Similarity	NPC139570
0.8737	High Similarity	NPC290481
0.8737	High Similarity	NPC473240
0.8723	High Similarity	NPC49776
0.8723	High Similarity	NPC214756
0.8723	High Similarity	NPC272075
0.8723	High Similarity	NPC63118
0.8723	High Similarity	NPC474436
0.8723	High Similarity	NPC295643
0.871	High Similarity	NPC46441
0.871	High Similarity	NPC474728
0.871	High Similarity	NPC113989
0.871	High Similarity	NPC120840
0.87	High Similarity	NPC477877
0.8696	High Similarity	NPC1753
0.8696	High Similarity	NPC474511
0.8681	High Similarity	NPC475862
0.8681	High Similarity	NPC74363
0.8681	High Similarity	NPC213412
0.8673	High Similarity	NPC118964

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 NPC261935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1809
0.2-0.3	3792
0.3-0.4	2214
0.4-0.5	687
0.5-0.6	227
0.6-0.7	192
0.7-0.8	25
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8817	High Similarity	NPD7515	Phase 2
0.8557	High Similarity	NPD7902	Approved
0.8438	Intermediate Similarity	NPD7748	Approved
0.8247	Intermediate Similarity	NPD7900	Approved
0.8247	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD7645	Phase 2
0.7857	Intermediate Similarity	NPD8035	Phase 2
0.7857	Intermediate Similarity	NPD8034	Phase 2
0.7807	Intermediate Similarity	NPD8328	Phase 3
0.7778	Intermediate Similarity	NPD6399	Phase 3
0.7757	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3618	Phase 1
0.7589	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7475	Intermediate Similarity	NPD5328	Approved
0.7474	Intermediate Similarity	NPD3667	Approved
0.7431	Intermediate Similarity	NPD6373	Approved
0.7431	Intermediate Similarity	NPD6372	Approved
0.7404	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD6881	Approved
0.7339	Intermediate Similarity	NPD6899	Approved
0.7339	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7320	Approved
0.7327	Intermediate Similarity	NPD6079	Approved
0.7308	Intermediate Similarity	NPD4755	Approved
0.73	Intermediate Similarity	NPD6101	Approved
0.73	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6649	Approved
0.7297	Intermediate Similarity	NPD6650	Approved
0.7263	Intermediate Similarity	NPD7525	Registered
0.7255	Intermediate Similarity	NPD4202	Approved
0.7248	Intermediate Similarity	NPD5701	Approved
0.7248	Intermediate Similarity	NPD5697	Approved
0.7238	Intermediate Similarity	NPD7638	Approved
0.7232	Intermediate Similarity	NPD8297	Approved
0.7212	Intermediate Similarity	NPD4697	Phase 3
0.7207	Intermediate Similarity	NPD7290	Approved
0.7207	Intermediate Similarity	NPD4634	Approved
0.7207	Intermediate Similarity	NPD6883	Approved
0.7207	Intermediate Similarity	NPD7102	Approved
0.72	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5286	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD4696	Approved
0.717	Intermediate Similarity	NPD4700	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.717	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7128	Intermediate Similarity	NPD6116	Phase 1
0.7117	Intermediate Similarity	NPD6013	Approved
0.7117	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6014	Approved
0.7117	Intermediate Similarity	NPD6012	Approved
0.7094	Intermediate Similarity	NPD6319	Approved
0.7091	Intermediate Similarity	NPD6412	Phase 2
0.708	Intermediate Similarity	NPD6882	Approved
0.7048	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5222	Approved
0.7048	Intermediate Similarity	NPD5221	Approved
0.7037	Intermediate Similarity	NPD5224	Approved
0.7037	Intermediate Similarity	NPD5211	Phase 2
0.7037	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD5226	Approved
0.7037	Intermediate Similarity	NPD4633	Approved
0.7027	Intermediate Similarity	NPD6011	Approved
0.7021	Intermediate Similarity	NPD6117	Approved
0.7018	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.6991	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5173	Approved
0.6972	Remote Similarity	NPD5174	Approved
0.6972	Remote Similarity	NPD5175	Approved
0.697	Remote Similarity	NPD3668	Phase 3
0.6967	Remote Similarity	NPD7736	Approved
0.6961	Remote Similarity	NPD4753	Phase 2
0.6944	Remote Similarity	NPD5223	Approved
0.6931	Remote Similarity	NPD3573	Approved
0.6923	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD5779	Approved
0.6916	Remote Similarity	NPD5696	Approved
0.6911	Remote Similarity	NPD7319	Approved
0.6909	Remote Similarity	NPD5141	Approved
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7614	Phase 1
0.6875	Remote Similarity	NPD6115	Approved
0.6875	Remote Similarity	NPD6697	Approved
0.6875	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD6118	Approved
0.6875	Remote Similarity	NPD6114	Approved
0.687	Remote Similarity	NPD8133	Approved
0.6863	Remote Similarity	NPD5737	Approved
0.6863	Remote Similarity	NPD6903	Approved
0.6863	Remote Similarity	NPD6672	Approved
0.686	Remote Similarity	NPD7492	Approved
0.6847	Remote Similarity	NPD4768	Approved
0.6847	Remote Similarity	NPD4767	Approved
0.6827	Remote Similarity	NPD5281	Approved
0.6827	Remote Similarity	NPD5284	Approved
0.6818	Remote Similarity	NPD4754	Approved
0.6809	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6803	Remote Similarity	NPD6616	Approved
0.6803	Remote Similarity	NPD7507	Approved
0.6792	Remote Similarity	NPD5210	Approved
0.6792	Remote Similarity	NPD5695	Phase 3
0.6792	Remote Similarity	NPD4629	Approved
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6274	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6748	Remote Similarity	NPD7078	Approved
0.6737	Remote Similarity	NPD6942	Approved
0.6737	Remote Similarity	NPD7339	Approved
0.6735	Remote Similarity	NPD4695	Discontinued
0.6726	Remote Similarity	NPD4730	Approved
0.6726	Remote Similarity	NPD4729	Approved
0.6726	Remote Similarity	NPD5128	Approved
0.6723	Remote Similarity	NPD7100	Approved
0.6723	Remote Similarity	NPD7101	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5279	Phase 3
0.6639	Remote Similarity	NPD6335	Approved
0.6637	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6921	Approved
0.6612	Remote Similarity	NPD8517	Approved
0.6612	Remote Similarity	NPD6909	Approved
0.6612	Remote Similarity	NPD8515	Approved
0.6612	Remote Similarity	NPD8516	Approved
0.6612	Remote Similarity	NPD6908	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6612	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD6868	Approved
0.6609	Remote Similarity	NPD5251	Approved
0.6609	Remote Similarity	NPD5249	Phase 3
0.6609	Remote Similarity	NPD5247	Approved
0.6609	Remote Similarity	NPD5248	Approved
0.6609	Remote Similarity	NPD5250	Approved
0.66	Remote Similarity	NPD4221	Approved
0.66	Remote Similarity	NPD4223	Phase 3
0.6583	Remote Similarity	NPD7516	Approved
0.6577	Remote Similarity	NPD7632	Discontinued
0.6574	Remote Similarity	NPD7732	Phase 3
0.6569	Remote Similarity	NPD5329	Approved
0.6557	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6317	Approved
0.6552	Remote Similarity	NPD5216	Approved
0.6552	Remote Similarity	NPD5215	Approved
0.6552	Remote Similarity	NPD5217	Approved
0.6535	Remote Similarity	NPD4788	Approved
0.6529	Remote Similarity	NPD8377	Approved
0.6529	Remote Similarity	NPD8294	Approved
0.6509	Remote Similarity	NPD7637	Suspended
0.6505	Remote Similarity	NPD6098	Approved
0.6504	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD7328	Approved
0.65	Remote Similarity	NPD5369	Approved
0.65	Remote Similarity	NPD7327	Approved
0.65	Remote Similarity	NPD6314	Approved
0.6476	Remote Similarity	NPD6673	Approved
0.6476	Remote Similarity	NPD6904	Approved
0.6476	Remote Similarity	NPD6080	Approved
0.6475	Remote Similarity	NPD8379	Approved
0.6475	Remote Similarity	NPD8335	Approved
0.6475	Remote Similarity	NPD8378	Approved
0.6475	Remote Similarity	NPD8296	Approved
0.6475	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8380	Approved
0.6475	Remote Similarity	NPD5983	Phase 2
0.6475	Remote Similarity	NPD8033	Approved
0.6471	Remote Similarity	NPD4197	Approved
0.6466	Remote Similarity	NPD5169	Approved
0.6466	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5135	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