NPASS Compound

Structure

CID244982 OpenBabel06191716042D 27 31 0 0 1 0 0 0 0 0999 V2000 1.6862 -2.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8792 3.1539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6857 -1.0060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3438 -1.9450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6854 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8434 1.4592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3707 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8428 0.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6859 -1.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5296 2.4311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8434 -1.4598 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5282 -1.4593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3710 0.9718 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8428 -0.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5294 1.4587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6862 0.9723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6860 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8431 -0.4864 0.0000 C 0 0 1 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 3.3709 -1.9454 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4808 2.6330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2373 1.4713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 15 1 0 0 0 0 3 21 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 15 26 2 0 0 0 0 16 23 1 6 0 0 0 17 25 1 6 0 0 0 18 20 1 0 0 0 0 18 27 1 1 0 0 0 19 22 1 1 0 0 0 19 24 1 0 0 0 0 20 21 1 6 0 0 0 21 22 1 6 0 0 0 22 4 1 1 0 0 0 23 24 1 1 0 0 0 24 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.28
Volume:	404.182
LogP:	2.392
LogD:	2.516
LogS:	-4.0
# Rotatable Bonds:	2
TPSA:	49.33
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.719
Synthetic Accessibility Score:	5.805
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.253
MDCK Permeability:	5.138117103342665e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.059
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.879
Plasma Protein Binding (PPB):	49.6295166015625%
Volume Distribution (VD):	1.456
Pgp-substrate:	52.14995193481445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.671
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.503

ADMET: Excretion

Clearance (CL):	8.14
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.381
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.506
Carcinogencity:	0.452
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC244982

Natural Product ID:	NPC244982
*Common Name:**	KTASKRCJBXZGMH-WMYNZDBHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KTASKRCJBXZGMH-WMYNZDBHSA-N
Standard InCHI:	InChI=1S/C24H37NO2/c1-14-16-6-7-19-22(4)12-18(27)20(15(2)26)21(22,3)10-11-24(19)13-23(16,24)9-8-17(14)25-5/h16-20,25,27H,1,6-13H2,2-5H3/t16-,17-,18+,19-,20-,21+,22-,23+,24-/m0/s1
SMILES:	CN[C@H]1CC[C@]23[C@H](C1=C)CC[C@@H]1[C@@]3(C2)CC[C@]2([C@@]1(C)C[C@H]([C@@H]2C(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3391816
PubChem CID:	12305373
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
NPO24301.1	Buxus microphylla var. sinica	Varieties	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24301.1	Buxus microphylla var. sinica	Varieties	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24059	Agathosma recurvifolia	Species	Rutaceae	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	57

Activity Type	# Activity
Cell Line	57

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.	63679.55	nM	PMID[475812]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	20417.38	nM	PMID[475812]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	62661.39	nM	PMID[475812]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	59020.11	nM	PMID[475812]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	71285.3	nM	PMID[475812]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	84918.05	nM	PMID[475812]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	56104.8	nM	PMID[475812]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	44977.99	nM	PMID[475812]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	63679.55	nM	PMID[475812]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	64268.77	nM	PMID[475812]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	49431.07	nM	PMID[475812]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	70307.23	nM	PMID[475812]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	77983.01	nM	PMID[475812]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	70469.31	nM	PMID[475812]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	59703.53	nM	PMID[475812]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	28444.61	nM	PMID[475812]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	80537.84	nM	PMID[475812]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	54827.7	nM	PMID[475812]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	21877.62	nM	PMID[475812]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[475812]

☑ 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 NPC244982 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	86
0.1-0.2	928
0.2-0.3	12357
0.3-0.4	14378
0.4-0.5	8777
0.5-0.6	5158
0.6-0.7	972
0.7-0.8	37
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476756
0.9394	High Similarity	NPC476755
0.8273	Intermediate Similarity	NPC124358
0.8208	Intermediate Similarity	NPC98765
0.7757	Intermediate Similarity	NPC135799
0.7723	Intermediate Similarity	NPC21035
0.7714	Intermediate Similarity	NPC174117
0.7619	Intermediate Similarity	NPC476754
0.7568	Intermediate Similarity	NPC195841
0.7568	Intermediate Similarity	NPC233256
0.7522	Intermediate Similarity	NPC473994
0.7455	Intermediate Similarity	NPC176012
0.7404	Intermediate Similarity	NPC135005
0.74	Intermediate Similarity	NPC46881
0.74	Intermediate Similarity	NPC477858
0.7395	Intermediate Similarity	NPC35037
0.7358	Intermediate Similarity	NPC476753
0.7358	Intermediate Similarity	NPC476752
0.7248	Intermediate Similarity	NPC474164
0.7228	Intermediate Similarity	NPC110780
0.7212	Intermediate Similarity	NPC134197
0.7207	Intermediate Similarity	NPC118275
0.7184	Intermediate Similarity	NPC76518
0.717	Intermediate Similarity	NPC312637
0.7168	Intermediate Similarity	NPC475239
0.7157	Intermediate Similarity	NPC245866
0.7143	Intermediate Similarity	NPC183374
0.7143	Intermediate Similarity	NPC211162
0.7143	Intermediate Similarity	NPC470592
0.7143	Intermediate Similarity	NPC146937
0.7143	Intermediate Similarity	NPC328313
0.7117	Intermediate Similarity	NPC239768
0.7117	Intermediate Similarity	NPC128698
0.7115	Intermediate Similarity	NPC70661
0.71	Intermediate Similarity	NPC201459
0.7087	Intermediate Similarity	NPC82902
0.708	Intermediate Similarity	NPC241879
0.7075	Intermediate Similarity	NPC116146
0.7075	Intermediate Similarity	NPC24772
0.7059	Intermediate Similarity	NPC145143
0.7048	Intermediate Similarity	NPC57469
0.7048	Intermediate Similarity	NPC43308
0.7019	Intermediate Similarity	NPC201655
0.7019	Intermediate Similarity	NPC102292
0.7019	Intermediate Similarity	NPC474218
0.7009	Intermediate Similarity	NPC84171
0.7	Intermediate Similarity	NPC234564
0.699	Remote Similarity	NPC21667
0.699	Remote Similarity	NPC291320
0.699	Remote Similarity	NPC472743
0.699	Remote Similarity	NPC472498
0.699	Remote Similarity	NPC471036
0.699	Remote Similarity	NPC475726
0.6983	Remote Similarity	NPC159367
0.6961	Remote Similarity	NPC103754
0.6961	Remote Similarity	NPC474484
0.6952	Remote Similarity	NPC469994
0.6952	Remote Similarity	NPC80590
0.6923	Remote Similarity	NPC475745
0.6923	Remote Similarity	NPC474482
0.6923	Remote Similarity	NPC147835
0.6923	Remote Similarity	NPC474233
0.6923	Remote Similarity	NPC95920
0.6923	Remote Similarity	NPC85001
0.6923	Remote Similarity	NPC263974
0.6923	Remote Similarity	NPC253645
0.6909	Remote Similarity	NPC266431
0.69	Remote Similarity	NPC106078
0.6893	Remote Similarity	NPC170985
0.6887	Remote Similarity	NPC317590
0.6887	Remote Similarity	NPC165895
0.687	Remote Similarity	NPC119329
0.6864	Remote Similarity	NPC472313
0.6863	Remote Similarity	NPC164999
0.6857	Remote Similarity	NPC292553
0.6857	Remote Similarity	NPC471034
0.6857	Remote Similarity	NPC190704
0.685	Remote Similarity	NPC317654
0.685	Remote Similarity	NPC96010
0.6847	Remote Similarity	NPC476903
0.6842	Remote Similarity	NPC58200
0.6827	Remote Similarity	NPC175410
0.6822	Remote Similarity	NPC471900
0.6822	Remote Similarity	NPC259252
0.681	Remote Similarity	NPC230677
0.6807	Remote Similarity	NPC66862
0.6792	Remote Similarity	NPC472738
0.6783	Remote Similarity	NPC470310
0.6762	Remote Similarity	NPC321187
0.6762	Remote Similarity	NPC227064
0.6762	Remote Similarity	NPC221758
0.6762	Remote Similarity	NPC85774
0.6762	Remote Similarity	NPC58841
0.6762	Remote Similarity	NPC214043
0.6762	Remote Similarity	NPC74595
0.6762	Remote Similarity	NPC59453
0.6762	Remote Similarity	NPC161423
0.6762	Remote Similarity	NPC329043
0.6762	Remote Similarity	NPC264665
0.6759	Remote Similarity	NPC213832
0.6759	Remote Similarity	NPC57954
0.6759	Remote Similarity	NPC477943
0.6759	Remote Similarity	NPC76879
0.6759	Remote Similarity	NPC2983
0.6757	Remote Similarity	NPC288906
0.6757	Remote Similarity	NPC205173
0.6757	Remote Similarity	NPC311164
0.6757	Remote Similarity	NPC272732
0.6757	Remote Similarity	NPC263135
0.675	Remote Similarity	NPC474452
0.6748	Remote Similarity	NPC474006
0.6735	Remote Similarity	NPC473267
0.6735	Remote Similarity	NPC110615
0.6729	Remote Similarity	NPC472495
0.6729	Remote Similarity	NPC259009
0.6729	Remote Similarity	NPC472497
0.6729	Remote Similarity	NPC472484
0.6729	Remote Similarity	NPC472481
0.6729	Remote Similarity	NPC4643
0.6729	Remote Similarity	NPC96496
0.6729	Remote Similarity	NPC472482
0.6727	Remote Similarity	NPC12722
0.6726	Remote Similarity	NPC220111
0.6723	Remote Similarity	NPC72753
0.672	Remote Similarity	NPC238323
0.6698	Remote Similarity	NPC182106
0.6698	Remote Similarity	NPC471224
0.6698	Remote Similarity	NPC294438
0.6698	Remote Similarity	NPC264317
0.6698	Remote Similarity	NPC311769
0.6697	Remote Similarity	NPC169933
0.6697	Remote Similarity	NPC320026
0.6697	Remote Similarity	NPC180849
0.6697	Remote Similarity	NPC261994
0.6697	Remote Similarity	NPC171441
0.6697	Remote Similarity	NPC149761
0.6697	Remote Similarity	NPC470378
0.6696	Remote Similarity	NPC29152
0.6696	Remote Similarity	NPC193934
0.6696	Remote Similarity	NPC271980
0.6695	Remote Similarity	NPC470595
0.6694	Remote Similarity	NPC475340
0.6667	Remote Similarity	NPC118800
0.6667	Remote Similarity	NPC265127
0.6667	Remote Similarity	NPC193360
0.6667	Remote Similarity	NPC53911
0.6667	Remote Similarity	NPC472739
0.6667	Remote Similarity	NPC55462
0.6667	Remote Similarity	NPC474719
0.6667	Remote Similarity	NPC310766
0.6667	Remote Similarity	NPC79238
0.6667	Remote Similarity	NPC471724
0.6667	Remote Similarity	NPC474459
0.6637	Remote Similarity	NPC473537
0.6637	Remote Similarity	NPC140300
0.6637	Remote Similarity	NPC156546
0.6636	Remote Similarity	NPC2783
0.6636	Remote Similarity	NPC278106
0.6636	Remote Similarity	NPC12774
0.6636	Remote Similarity	NPC299185
0.6636	Remote Similarity	NPC476168
0.6636	Remote Similarity	NPC98236
0.6636	Remote Similarity	NPC154101
0.6636	Remote Similarity	NPC51014
0.6636	Remote Similarity	NPC475416
0.6636	Remote Similarity	NPC269396
0.6636	Remote Similarity	NPC475007
0.6636	Remote Similarity	NPC145879
0.6636	Remote Similarity	NPC474778
0.6636	Remote Similarity	NPC474732
0.6636	Remote Similarity	NPC31564
0.6636	Remote Similarity	NPC472505
0.6636	Remote Similarity	NPC474733
0.6634	Remote Similarity	NPC20466
0.6609	Remote Similarity	NPC71706
0.6607	Remote Similarity	NPC476174
0.6607	Remote Similarity	NPC155985
0.6607	Remote Similarity	NPC263347
0.6607	Remote Similarity	NPC210214
0.6606	Remote Similarity	NPC122116
0.6606	Remote Similarity	NPC54689
0.6606	Remote Similarity	NPC472970
0.6606	Remote Similarity	NPC472971
0.6604	Remote Similarity	NPC146683
0.6604	Remote Similarity	NPC473246
0.6602	Remote Similarity	NPC192744
0.6602	Remote Similarity	NPC215843
0.6581	Remote Similarity	NPC470596
0.6579	Remote Similarity	NPC252564
0.6579	Remote Similarity	NPC475249
0.6577	Remote Similarity	NPC181594
0.6577	Remote Similarity	NPC471902
0.6577	Remote Similarity	NPC144739
0.6577	Remote Similarity	NPC473690
0.6577	Remote Similarity	NPC82138
0.6577	Remote Similarity	NPC59170
0.6577	Remote Similarity	NPC59350
0.6577	Remote Similarity	NPC287118
0.6574	Remote Similarity	NPC33768
0.6574	Remote Similarity	NPC93778

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 NPC244982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	81
0.1-0.2	642
0.2-0.3	3862
0.3-0.4	3446
0.4-0.5	694
0.5-0.6	350
0.6-0.7	74
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7157	Intermediate Similarity	NPD4788	Approved
0.6762	Remote Similarity	NPD3666	Approved
0.6762	Remote Similarity	NPD3665	Phase 1
0.6762	Remote Similarity	NPD4786	Approved
0.6762	Remote Similarity	NPD3133	Approved
0.6698	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6920	Discontinued
0.6637	Remote Similarity	NPD7920	Phase 3
0.6637	Remote Similarity	NPD7919	Phase 3
0.6633	Remote Similarity	NPD4245	Approved
0.6633	Remote Similarity	NPD4244	Approved
0.6579	Remote Similarity	NPD8088	Phase 1
0.6571	Remote Similarity	NPD3667	Approved
0.6555	Remote Similarity	NPD6415	Discontinued
0.6531	Remote Similarity	NPD3698	Phase 2
0.6522	Remote Similarity	NPD8418	Phase 2
0.6455	Remote Similarity	NPD5328	Approved
0.6455	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD4202	Approved
0.6415	Remote Similarity	NPD4221	Approved
0.6415	Remote Similarity	NPD4223	Phase 3
0.6404	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5329	Approved
0.6387	Remote Similarity	NPD7333	Discontinued
0.6339	Remote Similarity	NPD6079	Approved
0.633	Remote Similarity	NPD3618	Phase 1
0.63	Remote Similarity	NPD4789	Approved
0.6296	Remote Similarity	NPD4197	Approved
0.625	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7147	Phase 3
0.6228	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6083	Phase 2
0.6207	Remote Similarity	NPD6084	Phase 2
0.6207	Remote Similarity	NPD4755	Approved
0.6202	Remote Similarity	NPD6908	Approved
0.6202	Remote Similarity	NPD6909	Approved
0.62	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD8035	Phase 2
0.6195	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD7755	Approved
0.619	Remote Similarity	NPD7754	Approved
0.6182	Remote Similarity	NPD5279	Phase 3
0.6182	Remote Similarity	NPD5205	Approved
0.6182	Remote Similarity	NPD7334	Approved
0.6182	Remote Similarity	NPD4138	Approved
0.6182	Remote Similarity	NPD7146	Approved
0.6182	Remote Similarity	NPD4690	Approved
0.6182	Remote Similarity	NPD6684	Approved
0.6182	Remote Similarity	NPD6409	Approved
0.6182	Remote Similarity	NPD5330	Approved
0.6182	Remote Similarity	NPD4688	Approved
0.6182	Remote Similarity	NPD4693	Phase 3
0.6182	Remote Similarity	NPD4689	Approved
0.6182	Remote Similarity	NPD7521	Approved
0.6174	Remote Similarity	NPD4629	Approved
0.6174	Remote Similarity	NPD5210	Approved
0.616	Remote Similarity	NPD8298	Phase 2
0.614	Remote Similarity	NPD6399	Phase 3
0.6122	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4096	Approved
0.6102	Remote Similarity	NPD4700	Approved
0.6102	Remote Similarity	NPD5285	Approved
0.6102	Remote Similarity	NPD4696	Approved
0.6102	Remote Similarity	NPD5286	Approved
0.608	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7335	Phase 2
0.608	Remote Similarity	NPD7336	Phase 2
0.6074	Remote Similarity	NPD7751	Phase 1
0.6074	Remote Similarity	NPD6914	Discontinued
0.6071	Remote Similarity	NPD6903	Approved
0.605	Remote Similarity	NPD5223	Approved
0.6047	Remote Similarity	NPD7518	Approved
0.6047	Remote Similarity	NPD7519	Approved
0.6047	Remote Similarity	NPD7517	Approved
0.6036	Remote Similarity	NPD4694	Approved
0.6036	Remote Similarity	NPD5690	Phase 2
0.6036	Remote Similarity	NPD5280	Approved
0.6036	Remote Similarity	NPD8308	Discontinued
0.6036	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4139	Approved
0.6019	Remote Similarity	NPD4692	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD6117	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD6675	Approved
0.5984	Remote Similarity	NPD5739	Approved
0.5984	Remote Similarity	NPD7128	Approved
0.5984	Remote Similarity	NPD6402	Approved
0.5983	Remote Similarity	NPD5221	Approved
0.5983	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4697	Phase 3
0.5983	Remote Similarity	NPD5222	Approved
0.5952	Remote Similarity	NPD8077	Approved
0.5952	Remote Similarity	NPD8078	Approved
0.595	Remote Similarity	NPD5174	Approved
0.595	Remote Similarity	NPD4754	Approved
0.595	Remote Similarity	NPD5175	Approved
0.5943	Remote Similarity	NPD6116	Phase 1
0.5941	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5360	Phase 3
0.5935	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5173	Approved
0.5926	Remote Similarity	NPD7525	Registered
0.5922	Remote Similarity	NPD5777	Approved
0.592	Remote Similarity	NPD4634	Approved
0.5913	Remote Similarity	NPD7515	Phase 2
0.5905	Remote Similarity	NPD6942	Approved
0.5905	Remote Similarity	NPD7339	Approved
0.5905	Remote Similarity	NPD3703	Phase 2
0.5902	Remote Similarity	NPD5141	Approved
0.5897	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5695	Phase 3
0.5893	Remote Similarity	NPD6098	Approved
0.5888	Remote Similarity	NPD6697	Approved
0.5888	Remote Similarity	NPD6118	Approved
0.5888	Remote Similarity	NPD4777	Suspended
0.5888	Remote Similarity	NPD3617	Approved
0.5888	Remote Similarity	NPD6115	Approved
0.5888	Remote Similarity	NPD4776	Phase 2
0.5888	Remote Similarity	NPD6114	Approved
0.5887	Remote Similarity	NPD6881	Approved
0.5887	Remote Similarity	NPD7320	Approved
0.5887	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD5696	Approved
0.587	Remote Similarity	NPD8449	Approved
0.5865	Remote Similarity	NPD7604	Phase 2
0.5862	Remote Similarity	NPD5133	Approved
0.5854	Remote Similarity	NPD4767	Approved
0.5854	Remote Similarity	NPD4768	Approved
0.584	Remote Similarity	NPD6372	Approved
0.584	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD4195	Approved
0.5827	Remote Similarity	NPD8450	Suspended
0.5812	Remote Similarity	NPD5771	Approved
0.5806	Remote Similarity	NPD6412	Phase 2
0.5806	Remote Similarity	NPD5701	Approved
0.5806	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD6420	Discontinued
0.5794	Remote Similarity	NPD6883	Approved
0.5794	Remote Similarity	NPD7102	Approved
0.5794	Remote Similarity	NPD7290	Approved
0.5789	Remote Similarity	NPD6672	Approved
0.5789	Remote Similarity	NPD5737	Approved
0.5776	Remote Similarity	NPD5281	Approved
0.5776	Remote Similarity	NPD5284	Approved
0.5769	Remote Similarity	NPD4243	Approved
0.5769	Remote Similarity	NPD6081	Approved
0.576	Remote Similarity	NPD4729	Approved
0.576	Remote Similarity	NPD6011	Approved
0.576	Remote Similarity	NPD5128	Approved
0.576	Remote Similarity	NPD4730	Approved
0.5755	Remote Similarity	NPD3702	Approved
0.575	Remote Similarity	NPD7638	Approved
0.5748	Remote Similarity	NPD6617	Approved
0.5748	Remote Similarity	NPD8130	Phase 1
0.5748	Remote Similarity	NPD6650	Approved
0.5748	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6869	Approved
0.5748	Remote Similarity	NPD6847	Approved
0.5748	Remote Similarity	NPD6649	Approved
0.5743	Remote Similarity	NPD4224	Phase 2
0.5741	Remote Similarity	NPD3671	Phase 1
0.5739	Remote Similarity	NPD6904	Approved
0.5739	Remote Similarity	NPD6673	Approved
0.5739	Remote Similarity	NPD6080	Approved
0.5727	Remote Similarity	NPD857	Phase 3
0.5726	Remote Similarity	NPD8040	Discontinued
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5703	Remote Similarity	NPD6882	Approved
0.5703	Remote Similarity	NPD8297	Approved
0.5702	Remote Similarity	NPD7640	Approved
0.5702	Remote Similarity	NPD6404	Discontinued
0.5702	Remote Similarity	NPD7639	Approved
0.5688	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6001	Approved
0.5678	Remote Similarity	NPD7748	Approved
0.5669	Remote Similarity	NPD5251	Approved
0.5669	Remote Similarity	NPD5248	Approved
0.5669	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD5135	Approved
0.5669	Remote Similarity	NPD5169	Approved
0.5669	Remote Similarity	NPD5249	Phase 3
0.5669	Remote Similarity	NPD5250	Approved
0.5669	Remote Similarity	NPD5247	Approved
0.5664	Remote Similarity	NPD6334	Approved
0.5664	Remote Similarity	NPD6333	Approved
0.566	Remote Similarity	NPD6924	Approved
0.566	Remote Similarity	NPD4784	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