NPASS Compound

Structure

CID253645 OpenBabel06191716052D 30 35 0 0 1 0 0 0 0 0999 V2000 3.5827 -0.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3104 -2.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4137 -3.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8950 -2.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1181 -1.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2783 -1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1192 -4.6572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6010 -3.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2798 -4.1735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7613 -2.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9581 -3.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7596 0.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5782 -0.7834 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -1.5668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1186 -2.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9584 -4.1720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4391 -1.7511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4397 -2.7204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5994 -1.2669 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9209 -0.2992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9209 -1.2676 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2795 -3.2046 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7607 -1.7518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5692 -0.7834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0714 0.0865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8246 -4.6716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 5 6 1 0 0 0 0 5 18 2 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 17 24 1 0 0 0 0 17 27 1 1 0 0 0 18 25 1 0 0 0 0 19 29 1 6 0 0 0 20 6 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 6 0 0 0 22 26 1 6 0 0 0 23 14 1 6 0 0 0 23 24 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 6 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 27 12 1 6 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	413.33
Volume:	450.15
LogP:	5.169
LogD:	4.309
LogS:	-4.817
# Rotatable Bonds:	0
TPSA:	41.49
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	5.394
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.725
MDCK Permeability:	8.996881661005318e-06
Pgp-inhibitor:	0.319
Pgp-substrate:	0.941
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.718
Plasma Protein Binding (PPB):	75.9728012084961%
Volume Distribution (VD):	1.233
Pgp-substrate:	10.278600692749023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.505
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.091
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.785
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	11.7
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.884
Human Hepatotoxicity (H-HT):	0.412
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.944
Carcinogencity:	0.753
Eye Corrosion:	0.023
Eye Irritation:	0.013
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC253645

Natural Product ID:	NPC253645
*Common Name:**	KWVISVAMQJWJSZ-DXZIWIJNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KWVISVAMQJWJSZ-DXZIWIJNSA-N
Standard InCHI:	InChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16?,17-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1
SMILES:	CC1CC[C@@]2(NC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL372484
PubChem CID:	16061352
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0001704] Spirosolanes and derivatives

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	Whole plant	n.a.	steroidal saponins	PMID[16933867]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2211	Solanum nigrum	Species	Solanaceae	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
Ki	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4110	Individual Protein	3-beta-hydroxysteroid-delta(8),delta(7)-isomerase	Homo sapiens	Ki	>	100000.0	nM	PMID[454505]
NPT296	Individual Protein	Sigma opioid receptor	Homo sapiens	Ki	=	207.0	nM	PMID[454505]
NPT4111	Individual Protein	C-8 sterol isomerase	Saccharomyces cerevisiae S288c	Ki	=	1170.0	nM	PMID[454505]

☑ 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 NPC253645 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	101
0.1-0.2	926
0.2-0.3	10982
0.3-0.4	15565
0.4-0.5	8368
0.5-0.6	5720
0.6-0.7	971
0.7-0.8	46
0.8-0.85	10
0.85-0.9	1
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95920
1.0	High Similarity	NPC85001
1.0	High Similarity	NPC147835
0.9216	High Similarity	NPC212874
0.9208	High Similarity	NPC176012
0.8812	High Similarity	NPC474164
0.8431	Intermediate Similarity	NPC155985
0.8393	Intermediate Similarity	NPC304646
0.8393	Intermediate Similarity	NPC28280
0.8333	Intermediate Similarity	NPC15249
0.8333	Intermediate Similarity	NPC25455
0.8264	Intermediate Similarity	NPC122819
0.8197	Intermediate Similarity	NPC147753
0.8197	Intermediate Similarity	NPC150057
0.819	Intermediate Similarity	NPC91604
0.8165	Intermediate Similarity	NPC46981
0.7983	Intermediate Similarity	NPC296686
0.7966	Intermediate Similarity	NPC478138
0.7937	Intermediate Similarity	NPC287885
0.7864	Intermediate Similarity	NPC84171
0.7778	Intermediate Similarity	NPC135799
0.7719	Intermediate Similarity	NPC79238
0.7705	Intermediate Similarity	NPC317654
0.7705	Intermediate Similarity	NPC96010
0.7664	Intermediate Similarity	NPC289140
0.7549	Intermediate Similarity	NPC75810
0.7545	Intermediate Similarity	NPC118275
0.7436	Intermediate Similarity	NPC478137
0.7434	Intermediate Similarity	NPC233256
0.7434	Intermediate Similarity	NPC195841
0.7431	Intermediate Similarity	NPC140300
0.7328	Intermediate Similarity	NPC472313
0.7315	Intermediate Similarity	NPC243985
0.7315	Intermediate Similarity	NPC280710
0.7304	Intermediate Similarity	NPC159367
0.7281	Intermediate Similarity	NPC86906
0.7273	Intermediate Similarity	NPC35037
0.7273	Intermediate Similarity	NPC240650
0.7265	Intermediate Similarity	NPC474459
0.7257	Intermediate Similarity	NPC98765
0.7231	Intermediate Similarity	NPC297058
0.7222	Intermediate Similarity	NPC242419
0.7222	Intermediate Similarity	NPC235126
0.7203	Intermediate Similarity	NPC474452
0.72	Intermediate Similarity	NPC477522
0.7193	Intermediate Similarity	NPC475239
0.7182	Intermediate Similarity	NPC476903
0.7179	Intermediate Similarity	NPC287764
0.7168	Intermediate Similarity	NPC50815
0.7109	Intermediate Similarity	NPC478139
0.7105	Intermediate Similarity	NPC241879
0.7091	Intermediate Similarity	NPC272732
0.7091	Intermediate Similarity	NPC311164
0.7087	Intermediate Similarity	NPC5985
0.7087	Intermediate Similarity	NPC478136
0.7064	Intermediate Similarity	NPC93027
0.7063	Intermediate Similarity	NPC48886
0.7063	Intermediate Similarity	NPC265275
0.7063	Intermediate Similarity	NPC94881
0.7059	Intermediate Similarity	NPC26117
0.7054	Intermediate Similarity	NPC40488
0.7048	Intermediate Similarity	NPC474189
0.7048	Intermediate Similarity	NPC474349
0.7018	Intermediate Similarity	NPC247060
0.7	Intermediate Similarity	NPC321381
0.7	Intermediate Similarity	NPC96319
0.7	Intermediate Similarity	NPC107059
0.7	Intermediate Similarity	NPC321016
0.6991	Remote Similarity	NPC239768
0.6991	Remote Similarity	NPC128698
0.6984	Remote Similarity	NPC476503
0.6983	Remote Similarity	NPC477292
0.6964	Remote Similarity	NPC177818
0.6961	Remote Similarity	NPC1319
0.6957	Remote Similarity	NPC293299
0.6957	Remote Similarity	NPC45365
0.6952	Remote Similarity	NPC209802
0.694	Remote Similarity	NPC478140
0.6931	Remote Similarity	NPC318495
0.6931	Remote Similarity	NPC155986
0.6931	Remote Similarity	NPC198968
0.6923	Remote Similarity	NPC1272
0.6923	Remote Similarity	NPC476756
0.6923	Remote Similarity	NPC470614
0.6923	Remote Similarity	NPC244982
0.6917	Remote Similarity	NPC476498
0.69	Remote Similarity	NPC22105
0.69	Remote Similarity	NPC285893
0.69	Remote Similarity	NPC304309
0.69	Remote Similarity	NPC28657
0.69	Remote Similarity	NPC230301
0.69	Remote Similarity	NPC136188
0.69	Remote Similarity	NPC134847
0.69	Remote Similarity	NPC288035
0.69	Remote Similarity	NPC162742
0.6893	Remote Similarity	NPC12035
0.688	Remote Similarity	NPC476504
0.687	Remote Similarity	NPC471083
0.6863	Remote Similarity	NPC477514
0.6863	Remote Similarity	NPC87604
0.6863	Remote Similarity	NPC473943
0.6863	Remote Similarity	NPC474216
0.6832	Remote Similarity	NPC113733
0.6832	Remote Similarity	NPC240604
0.6832	Remote Similarity	NPC300324
0.6827	Remote Similarity	NPC474731
0.6827	Remote Similarity	NPC474752
0.6827	Remote Similarity	NPC474683
0.6827	Remote Similarity	NPC82986
0.6827	Remote Similarity	NPC474759
0.6827	Remote Similarity	NPC7505
0.6822	Remote Similarity	NPC24277
0.6803	Remote Similarity	NPC476499
0.6796	Remote Similarity	NPC328714
0.6796	Remote Similarity	NPC28862
0.6796	Remote Similarity	NPC109546
0.6796	Remote Similarity	NPC47982
0.6796	Remote Similarity	NPC84694
0.6796	Remote Similarity	NPC143182
0.6796	Remote Similarity	NPC81306
0.6792	Remote Similarity	NPC124172
0.6786	Remote Similarity	NPC470382
0.6786	Remote Similarity	NPC471635
0.6786	Remote Similarity	NPC174117
0.6786	Remote Similarity	NPC25033
0.6786	Remote Similarity	NPC476261
0.6786	Remote Similarity	NPC119225
0.6783	Remote Similarity	NPC176406
0.6783	Remote Similarity	NPC474022
0.6777	Remote Similarity	NPC477291
0.6777	Remote Similarity	NPC124358
0.6765	Remote Similarity	NPC34019
0.6762	Remote Similarity	NPC201852
0.6762	Remote Similarity	NPC20853
0.6757	Remote Similarity	NPC98193
0.6752	Remote Similarity	NPC119329
0.6733	Remote Similarity	NPC257347
0.6733	Remote Similarity	NPC471723
0.6733	Remote Similarity	NPC141071
0.6731	Remote Similarity	NPC164840
0.6731	Remote Similarity	NPC234193
0.6731	Remote Similarity	NPC241290
0.6731	Remote Similarity	NPC209944
0.6718	Remote Similarity	NPC201359
0.6699	Remote Similarity	NPC18603
0.6699	Remote Similarity	NPC76931
0.6699	Remote Similarity	NPC307965
0.6699	Remote Similarity	NPC275910
0.6698	Remote Similarity	NPC475789
0.6697	Remote Similarity	NPC470542
0.6697	Remote Similarity	NPC471952
0.6667	Remote Similarity	NPC474531
0.6667	Remote Similarity	NPC474970
0.6667	Remote Similarity	NPC264245
0.6667	Remote Similarity	NPC47761
0.6667	Remote Similarity	NPC118329
0.6667	Remote Similarity	NPC152039
0.6667	Remote Similarity	NPC474583
0.6667	Remote Similarity	NPC23852
0.6667	Remote Similarity	NPC189883
0.6667	Remote Similarity	NPC129165
0.6667	Remote Similarity	NPC475701
0.6667	Remote Similarity	NPC134330
0.6667	Remote Similarity	NPC209620
0.6667	Remote Similarity	NPC152808
0.6667	Remote Similarity	NPC293287
0.6667	Remote Similarity	NPC329782
0.6667	Remote Similarity	NPC470383
0.6639	Remote Similarity	NPC25340
0.6639	Remote Similarity	NPC169375
0.6636	Remote Similarity	NPC474047
0.6636	Remote Similarity	NPC105495
0.6635	Remote Similarity	NPC30986
0.6635	Remote Similarity	NPC209430
0.661	Remote Similarity	NPC474464
0.6609	Remote Similarity	NPC309493
0.6606	Remote Similarity	NPC271967
0.6606	Remote Similarity	NPC21035
0.6604	Remote Similarity	NPC248886
0.6604	Remote Similarity	NPC50964
0.6604	Remote Similarity	NPC49964
0.6604	Remote Similarity	NPC472312
0.6604	Remote Similarity	NPC470049
0.6604	Remote Similarity	NPC189972
0.6604	Remote Similarity	NPC101462
0.6602	Remote Similarity	NPC214570
0.6579	Remote Similarity	NPC253115
0.6579	Remote Similarity	NPC304899
0.6574	Remote Similarity	NPC266511
0.6574	Remote Similarity	NPC157257
0.6574	Remote Similarity	NPC318390
0.6574	Remote Similarity	NPC274448
0.6571	Remote Similarity	NPC236112
0.6562	Remote Similarity	NPC469943
0.6555	Remote Similarity	NPC474015
0.6555	Remote Similarity	NPC181845
0.6552	Remote Similarity	NPC83709
0.6545	Remote Similarity	NPC2158
0.6545	Remote Similarity	NPC328313
0.6542	Remote Similarity	NPC110778

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 NPC253645 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	514
0.2-0.3	3413
0.3-0.4	3739
0.4-0.5	1020
0.5-0.6	317
0.6-0.7	45
0.7-0.8	3
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8264	Intermediate Similarity	NPD8449	Approved
0.8197	Intermediate Similarity	NPD8450	Suspended
0.7203	Intermediate Similarity	NPD7337	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7335	Phase 2
0.7203	Intermediate Similarity	NPD7336	Phase 2
0.7	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD7339	Approved
0.6613	Remote Similarity	NPD7755	Approved
0.6613	Remote Similarity	NPD7754	Approved
0.6481	Remote Similarity	NPD4786	Approved
0.6471	Remote Similarity	NPD4785	Approved
0.6471	Remote Similarity	NPD4784	Approved
0.6455	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4243	Approved
0.6435	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7333	Discontinued
0.6415	Remote Similarity	NPD7525	Registered
0.6379	Remote Similarity	NPD7919	Phase 3
0.6379	Remote Similarity	NPD7920	Phase 3
0.6364	Remote Similarity	NPD8308	Discontinued
0.6325	Remote Similarity	NPD8088	Phase 1
0.6321	Remote Similarity	NPD7645	Phase 2
0.6311	Remote Similarity	NPD6926	Approved
0.6311	Remote Similarity	NPD6924	Approved
0.6296	Remote Similarity	NPD3667	Approved
0.6262	Remote Similarity	NPD4748	Discontinued
0.6231	Remote Similarity	NPD6909	Approved
0.6231	Remote Similarity	NPD6908	Approved
0.6207	Remote Similarity	NPD7991	Discontinued
0.619	Remote Similarity	NPD6933	Approved
0.6182	Remote Similarity	NPD3666	Approved
0.6182	Remote Similarity	NPD3665	Phase 1
0.6182	Remote Similarity	NPD3133	Approved
0.6174	Remote Similarity	NPD6399	Phase 3
0.6117	Remote Similarity	NPD7152	Approved
0.6117	Remote Similarity	NPD7151	Approved
0.6117	Remote Similarity	NPD7150	Approved
0.6106	Remote Similarity	NPD4723	Approved
0.6106	Remote Similarity	NPD4722	Approved
0.6098	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5275	Approved
0.6095	Remote Similarity	NPD4190	Phase 3
0.6091	Remote Similarity	NPD6695	Phase 3
0.6078	Remote Similarity	NPD6923	Approved
0.6078	Remote Similarity	NPD6922	Approved
0.6053	Remote Similarity	NPD5328	Approved
0.6036	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD4195	Approved
0.6019	Remote Similarity	NPD6929	Approved
0.6019	Remote Similarity	NPD7143	Approved
0.6019	Remote Similarity	NPD7144	Approved
0.5984	Remote Similarity	NPD8078	Approved
0.5984	Remote Similarity	NPD8077	Approved
0.5966	Remote Similarity	NPD6083	Phase 2
0.5966	Remote Similarity	NPD6084	Phase 2
0.5965	Remote Similarity	NPD6903	Approved
0.5965	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6930	Phase 2
0.5963	Remote Similarity	NPD6931	Approved
0.5954	Remote Similarity	NPD7517	Approved
0.5954	Remote Similarity	NPD7518	Approved
0.5954	Remote Similarity	NPD7519	Approved
0.595	Remote Similarity	NPD4159	Approved
0.5948	Remote Similarity	NPD6079	Approved
0.5929	Remote Similarity	NPD7521	Approved
0.5929	Remote Similarity	NPD7146	Approved
0.5929	Remote Similarity	NPD6409	Approved
0.5929	Remote Similarity	NPD5330	Approved
0.5929	Remote Similarity	NPD6684	Approved
0.5929	Remote Similarity	NPD7334	Approved
0.5929	Remote Similarity	NPD3618	Phase 1
0.592	Remote Similarity	NPD7320	Approved
0.5913	Remote Similarity	NPD6051	Approved
0.5913	Remote Similarity	NPD4753	Phase 2
0.5896	Remote Similarity	NPD7122	Discontinued
0.5887	Remote Similarity	NPD7128	Approved
0.5887	Remote Similarity	NPD6675	Approved
0.5887	Remote Similarity	NPD5739	Approved
0.5887	Remote Similarity	NPD6920	Discontinued
0.5887	Remote Similarity	NPD6402	Approved
0.5877	Remote Similarity	NPD7524	Approved
0.5877	Remote Similarity	NPD7750	Discontinued
0.5856	Remote Similarity	NPD4223	Phase 3
0.5856	Remote Similarity	NPD4221	Approved
0.5847	Remote Similarity	NPD5771	Approved
0.5847	Remote Similarity	NPD5707	Approved
0.5841	Remote Similarity	NPD5329	Approved
0.584	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD6932	Approved
0.5833	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD5776	Phase 2
0.5833	Remote Similarity	NPD6925	Approved
0.5818	Remote Similarity	NPD6928	Phase 2
0.5818	Remote Similarity	NPD7509	Discontinued
0.5794	Remote Similarity	NPD6899	Approved
0.5794	Remote Similarity	NPD6881	Approved
0.5794	Remote Similarity	NPD6415	Discontinued
0.5785	Remote Similarity	NPD7638	Approved
0.578	Remote Similarity	NPD7145	Approved
0.5772	Remote Similarity	NPD8131	Suspended
0.5755	Remote Similarity	NPD7751	Phase 1
0.5752	Remote Similarity	NPD3668	Phase 3
0.5752	Remote Similarity	NPD4197	Approved
0.5748	Remote Similarity	NPD6373	Approved
0.5748	Remote Similarity	NPD6372	Approved
0.5743	Remote Similarity	NPD3638	Discontinued
0.5738	Remote Similarity	NPD4696	Approved
0.5738	Remote Similarity	NPD5286	Approved
0.5738	Remote Similarity	NPD7640	Approved
0.5738	Remote Similarity	NPD7639	Approved
0.5738	Remote Similarity	NPD5285	Approved
0.5738	Remote Similarity	NPD4700	Approved
0.5727	Remote Similarity	NPD6683	Phase 2
0.5726	Remote Similarity	NPD7911	Approved
0.5726	Remote Similarity	NPD7912	Approved
0.5726	Remote Similarity	NPD7987	Approved
0.5726	Remote Similarity	NPD7986	Approved
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD5701	Approved
0.5704	Remote Similarity	NPD7725	Approved
0.5703	Remote Similarity	NPD6883	Approved
0.5703	Remote Similarity	NPD6420	Discontinued
0.5703	Remote Similarity	NPD7290	Approved
0.5703	Remote Similarity	NPD7102	Approved
0.5702	Remote Similarity	NPD6893	Approved
0.5702	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD6333	Approved
0.5694	Remote Similarity	NPD6334	Approved
0.5691	Remote Similarity	NPD5223	Approved
0.5682	Remote Similarity	NPD4031	Approved
0.5682	Remote Similarity	NPD4032	Approved
0.5678	Remote Similarity	NPD7087	Discontinued
0.5676	Remote Similarity	NPD7514	Phase 3
0.5672	Remote Similarity	NPD7147	Phase 3
0.5672	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6011	Approved
0.5667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5210	Approved
0.5667	Remote Similarity	NPD5695	Phase 3
0.5667	Remote Similarity	NPD4629	Approved
0.5664	Remote Similarity	NPD4788	Approved
0.5659	Remote Similarity	NPD6869	Approved
0.5659	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD6847	Approved
0.5659	Remote Similarity	NPD6617	Approved
0.5659	Remote Similarity	NPD8130	Phase 1
0.5659	Remote Similarity	NPD6649	Approved
0.5659	Remote Similarity	NPD6650	Approved
0.5656	Remote Similarity	NPD5696	Approved
0.5652	Remote Similarity	NPD5205	Approved
0.5652	Remote Similarity	NPD4688	Approved
0.5652	Remote Similarity	NPD6098	Approved
0.5652	Remote Similarity	NPD4693	Phase 3
0.5652	Remote Similarity	NPD4689	Approved
0.5652	Remote Similarity	NPD4138	Approved
0.5652	Remote Similarity	NPD4690	Approved
0.5652	Remote Similarity	NPD5279	Phase 3
0.5645	Remote Similarity	NPD5225	Approved
0.5645	Remote Similarity	NPD5224	Approved
0.5645	Remote Similarity	NPD5211	Phase 2
0.5645	Remote Similarity	NPD5226	Approved
0.5645	Remote Similarity	NPD4633	Approved
0.5643	Remote Similarity	NPD6914	Discontinued
0.5639	Remote Similarity	NPD7327	Approved
0.5639	Remote Similarity	NPD7328	Approved
0.5636	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6008	Approved
0.5635	Remote Similarity	NPD8040	Discontinued
0.5635	Remote Similarity	NPD6640	Phase 3
0.563	Remote Similarity	NPD8033	Approved
0.5625	Remote Similarity	NPD6012	Approved
0.5625	Remote Similarity	NPD6014	Approved
0.5625	Remote Similarity	NPD6013	Approved
0.5625	Remote Similarity	NPD6902	Approved
0.562	Remote Similarity	NPD5221	Approved
0.562	Remote Similarity	NPD4697	Phase 3
0.562	Remote Similarity	NPD5222	Approved
0.562	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD6429	Approved
0.5615	Remote Similarity	NPD8297	Approved
0.5615	Remote Similarity	NPD6430	Approved
0.5615	Remote Similarity	NPD6882	Approved
0.56	Remote Similarity	NPD4754	Approved
0.56	Remote Similarity	NPD5175	Approved
0.56	Remote Similarity	NPD5174	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