NPASS Compound

Structure

CID35037 OpenBabel06191715362D 26 30 0 0 1 0 0 0 0 0999 V2000 -1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -4.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -4.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 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 2 21 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 15 1 0 0 0 0 5 17 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 1 1 6 0 0 0 12 15 1 0 0 0 0 12 26 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 6 0 0 0 15 22 1 6 0 0 0 16 19 1 0 0 0 0 16 21 1 6 0 0 0 17 19 1 0 0 0 0 17 22 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	359.25
Volume:	378.38
LogP:	2.239
LogD:	2.365
LogS:	-3.508
# Rotatable Bonds:	1
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	5.364
Fsp3:	0.864
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:	-4.759
MDCK Permeability:	3.506441134959459e-05
Pgp-inhibitor:	0.632
Pgp-substrate:	0.778
Human Intestinal Absorption (HIA):	0.762
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.161

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815
Plasma Protein Binding (PPB):	51.0714225769043%
Volume Distribution (VD):	1.026
Pgp-substrate:	45.39124298095703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.198
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.496
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	11.079
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.546
Human Hepatotoxicity (H-HT):	0.575
Drug-inuced Liver Injury (DILI):	0.418
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.868
Carcinogencity:	0.854
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC35037

Natural Product ID:	NPC35037
*Common Name:**	PSCHPNOCVHDNMF-RZOBYWFHSA-N
IUPAC Name:	n.a.
Synonyms:	7Alpha-Hydroxyparavallarine
Standard InCHIKey:	PSCHPNOCVHDNMF-RZOBYWFHSA-N
Standard InCHI:	InChI=1S/C22H33NO3/c1-12-15-4-5-17-19-16(7-9-22(15,17)20(25)26-12)21(2)8-6-14(23-3)10-13(21)11-18(19)24/h11-12,14-19,23-24H,4-10H2,1-3H3/t12-,14-,15+,16-,17-,18+,19+,21-,22-/m0/s1
SMILES:	CN[C@H]1CC[C@]2(C(=C[C@H]([C@@H]3[C@@H]2CC[C@]24[C@H]3CC[C@@H]4[C@@H](OC2=O)C)O)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801973
PubChem CID:	56683357
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443172]
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21443172]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[568409]

☑ 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 NPC35037 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	93
0.1-0.2	653
0.2-0.3	3250
0.3-0.4	16985
0.4-0.5	9854
0.5-0.6	8759
0.6-0.7	3008
0.7-0.8	88
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8899	High Similarity	NPC195841
0.8899	High Similarity	NPC233256
0.844	Intermediate Similarity	NPC128698
0.844	Intermediate Similarity	NPC239768
0.8214	Intermediate Similarity	NPC98765
0.8142	Intermediate Similarity	NPC119329
0.7731	Intermediate Similarity	NPC79238
0.7647	Intermediate Similarity	NPC472313
0.7632	Intermediate Similarity	NPC218383
0.7611	Intermediate Similarity	NPC475894
0.7586	Intermediate Similarity	NPC140723
0.7586	Intermediate Similarity	NPC36688
0.7583	Intermediate Similarity	NPC474459
0.7578	Intermediate Similarity	NPC96010
0.7578	Intermediate Similarity	NPC317654
0.7544	Intermediate Similarity	NPC271387
0.7544	Intermediate Similarity	NPC153792
0.7538	Intermediate Similarity	NPC478139
0.7521	Intermediate Similarity	NPC474452
0.75	Intermediate Similarity	NPC63511
0.75	Intermediate Similarity	NPC237286
0.7458	Intermediate Similarity	NPC96377
0.7411	Intermediate Similarity	NPC470224
0.7395	Intermediate Similarity	NPC59530
0.7395	Intermediate Similarity	NPC476756
0.7395	Intermediate Similarity	NPC244982
0.7373	Intermediate Similarity	NPC255309
0.7373	Intermediate Similarity	NPC471293
0.7339	Intermediate Similarity	NPC49492
0.7339	Intermediate Similarity	NPC266728
0.7311	Intermediate Similarity	NPC86906
0.7304	Intermediate Similarity	NPC474164
0.7295	Intermediate Similarity	NPC66862
0.7273	Intermediate Similarity	NPC201359
0.7273	Intermediate Similarity	NPC167877
0.7273	Intermediate Similarity	NPC85001
0.7273	Intermediate Similarity	NPC147835
0.7273	Intermediate Similarity	NPC253645
0.7273	Intermediate Similarity	NPC95920
0.7266	Intermediate Similarity	NPC478138
0.7258	Intermediate Similarity	NPC474181
0.7252	Intermediate Similarity	NPC478136
0.7213	Intermediate Similarity	NPC72753
0.7203	Intermediate Similarity	NPC136289
0.7203	Intermediate Similarity	NPC176012
0.72	Intermediate Similarity	NPC28280
0.72	Intermediate Similarity	NPC304646
0.7193	Intermediate Similarity	NPC250075
0.7188	Intermediate Similarity	NPC242692
0.7179	Intermediate Similarity	NPC471041
0.7179	Intermediate Similarity	NPC476274
0.7177	Intermediate Similarity	NPC962
0.7167	Intermediate Similarity	NPC230677
0.7167	Intermediate Similarity	NPC196528
0.7156	Intermediate Similarity	NPC165064
0.7155	Intermediate Similarity	NPC107243
0.7143	Intermediate Similarity	NPC474775
0.713	Intermediate Similarity	NPC469599
0.7119	Intermediate Similarity	NPC476240
0.7119	Intermediate Similarity	NPC476223
0.7119	Intermediate Similarity	NPC224720
0.7119	Intermediate Similarity	NPC81530
0.7119	Intermediate Similarity	NPC472924
0.7119	Intermediate Similarity	NPC474327
0.7109	Intermediate Similarity	NPC109973
0.7107	Intermediate Similarity	NPC230541
0.7107	Intermediate Similarity	NPC473037
0.7107	Intermediate Similarity	NPC110496
0.7105	Intermediate Similarity	NPC470254
0.7105	Intermediate Similarity	NPC477855
0.7097	Intermediate Similarity	NPC124358
0.7097	Intermediate Similarity	NPC126691
0.7097	Intermediate Similarity	NPC276995
0.7097	Intermediate Similarity	NPC76660
0.7094	Intermediate Similarity	NPC23364
0.7091	Intermediate Similarity	NPC471224
0.7091	Intermediate Similarity	NPC470223
0.7087	Intermediate Similarity	NPC9714
0.7083	Intermediate Similarity	NPC475239
0.708	Intermediate Similarity	NPC232202
0.708	Intermediate Similarity	NPC84171
0.7069	Intermediate Similarity	NPC328371
0.7069	Intermediate Similarity	NPC322063
0.7069	Intermediate Similarity	NPC42042
0.7059	Intermediate Similarity	NPC471083
0.7054	Intermediate Similarity	NPC28227
0.7049	Intermediate Similarity	NPC189075
0.7049	Intermediate Similarity	NPC275539
0.7049	Intermediate Similarity	NPC472217
0.7049	Intermediate Similarity	NPC472219
0.7049	Intermediate Similarity	NPC472218
0.7043	Intermediate Similarity	NPC471720
0.7043	Intermediate Similarity	NPC184870
0.704	Intermediate Similarity	NPC312017
0.704	Intermediate Similarity	NPC9848
0.704	Intermediate Similarity	NPC52634
0.704	Intermediate Similarity	NPC250109
0.7034	Intermediate Similarity	NPC477521
0.7034	Intermediate Similarity	NPC135799
0.7034	Intermediate Similarity	NPC287833
0.7034	Intermediate Similarity	NPC167974
0.7034	Intermediate Similarity	NPC51370
0.7027	Intermediate Similarity	NPC155011
0.7025	Intermediate Similarity	NPC231530
0.7025	Intermediate Similarity	NPC236644
0.7025	Intermediate Similarity	NPC278628
0.7025	Intermediate Similarity	NPC127609
0.7018	Intermediate Similarity	NPC107690
0.7018	Intermediate Similarity	NPC234335
0.7018	Intermediate Similarity	NPC471747
0.7018	Intermediate Similarity	NPC154101
0.7009	Intermediate Similarity	NPC121339
0.7009	Intermediate Similarity	NPC57416
0.7	Intermediate Similarity	NPC472458
0.7	Intermediate Similarity	NPC236390
0.7	Intermediate Similarity	NPC476237
0.7	Intermediate Similarity	NPC100391
0.7	Intermediate Similarity	NPC222688
0.6992	Remote Similarity	NPC218602
0.6992	Remote Similarity	NPC141350
0.6984	Remote Similarity	NPC471398
0.6984	Remote Similarity	NPC326542
0.6983	Remote Similarity	NPC469995
0.6983	Remote Similarity	NPC174948
0.6983	Remote Similarity	NPC271195
0.6983	Remote Similarity	NPC173875
0.6983	Remote Similarity	NPC318282
0.6983	Remote Similarity	NPC279974
0.6975	Remote Similarity	NPC39683
0.6964	Remote Similarity	NPC474684
0.6964	Remote Similarity	NPC142361
0.696	Remote Similarity	NPC207251
0.696	Remote Similarity	NPC469968
0.696	Remote Similarity	NPC80834
0.6957	Remote Similarity	NPC206810
0.6953	Remote Similarity	NPC476952
0.6949	Remote Similarity	NPC119036
0.6949	Remote Similarity	NPC197386
0.6949	Remote Similarity	NPC477854
0.6942	Remote Similarity	NPC164835
0.6942	Remote Similarity	NPC228669
0.6942	Remote Similarity	NPC29705
0.6937	Remote Similarity	NPC474083
0.6937	Remote Similarity	NPC52628
0.6937	Remote Similarity	NPC283733
0.6935	Remote Similarity	NPC272898
0.6935	Remote Similarity	NPC473036
0.6935	Remote Similarity	NPC76084
0.693	Remote Similarity	NPC471896
0.6929	Remote Similarity	NPC148458
0.6929	Remote Similarity	NPC165396
0.6929	Remote Similarity	NPC196931
0.6923	Remote Similarity	NPC54248
0.6923	Remote Similarity	NPC58052
0.6923	Remote Similarity	NPC173272
0.6923	Remote Similarity	NPC7124
0.6923	Remote Similarity	NPC276103
0.6923	Remote Similarity	NPC111684
0.6923	Remote Similarity	NPC3772
0.6917	Remote Similarity	NPC204450
0.6917	Remote Similarity	NPC195290
0.6917	Remote Similarity	NPC476755
0.6917	Remote Similarity	NPC234892
0.6917	Remote Similarity	NPC293753
0.6917	Remote Similarity	NPC50815
0.6911	Remote Similarity	NPC94529
0.6909	Remote Similarity	NPC21667
0.6906	Remote Similarity	NPC287885
0.6905	Remote Similarity	NPC472926
0.6899	Remote Similarity	NPC475041
0.6897	Remote Similarity	NPC470957
0.6897	Remote Similarity	NPC469406
0.6897	Remote Similarity	NPC470958
0.6897	Remote Similarity	NPC474922
0.6894	Remote Similarity	NPC296686
0.6894	Remote Similarity	NPC8369
0.6891	Remote Similarity	NPC201406
0.6891	Remote Similarity	NPC251680
0.6891	Remote Similarity	NPC241221
0.6891	Remote Similarity	NPC307954
0.6885	Remote Similarity	NPC469607
0.688	Remote Similarity	NPC118860
0.688	Remote Similarity	NPC214797
0.688	Remote Similarity	NPC231589
0.6875	Remote Similarity	NPC470051
0.6875	Remote Similarity	NPC284068
0.6875	Remote Similarity	NPC469994
0.6875	Remote Similarity	NPC322159
0.6875	Remote Similarity	NPC470050
0.6875	Remote Similarity	NPC472927
0.6864	Remote Similarity	NPC106557
0.6864	Remote Similarity	NPC320306
0.686	Remote Similarity	NPC222153
0.686	Remote Similarity	NPC478057
0.6855	Remote Similarity	NPC286174
0.6855	Remote Similarity	NPC258543
0.6855	Remote Similarity	NPC257082
0.6855	Remote Similarity	NPC77947
0.6855	Remote Similarity	NPC143706
0.6855	Remote Similarity	NPC472534

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 NPC35037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	82
0.1-0.2	476
0.2-0.3	2732
0.3-0.4	3871
0.4-0.5	1385
0.5-0.6	433
0.6-0.7	170
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
0.7217	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6914	Discontinued
0.6957	Remote Similarity	NPD6399	Phase 3
0.6891	Remote Similarity	NPD7640	Approved
0.6891	Remote Similarity	NPD7639	Approved
0.6885	Remote Similarity	NPD7333	Discontinued
0.6807	Remote Similarity	NPD7638	Approved
0.6794	Remote Similarity	NPD6908	Approved
0.6794	Remote Similarity	NPD6909	Approved
0.6788	Remote Similarity	NPD6845	Suspended
0.6769	Remote Similarity	NPD7518	Approved
0.6769	Remote Similarity	NPD7517	Approved
0.6769	Remote Similarity	NPD7519	Approved
0.6748	Remote Similarity	NPD6008	Approved
0.6718	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7147	Phase 3
0.6696	Remote Similarity	NPD5328	Approved
0.6696	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD8449	Approved
0.664	Remote Similarity	NPD7320	Approved
0.6619	Remote Similarity	NPD8450	Suspended
0.6613	Remote Similarity	NPD7128	Approved
0.6613	Remote Similarity	NPD6402	Approved
0.6613	Remote Similarity	NPD5739	Approved
0.6613	Remote Similarity	NPD6675	Approved
0.6612	Remote Similarity	NPD6404	Discontinued
0.6609	Remote Similarity	NPD6903	Approved
0.6594	Remote Similarity	NPD7260	Phase 2
0.6587	Remote Similarity	NPD6372	Approved
0.6587	Remote Similarity	NPD6373	Approved
0.6583	Remote Similarity	NPD6083	Phase 2
0.6583	Remote Similarity	NPD6084	Phase 2
0.6581	Remote Similarity	NPD6079	Approved
0.6579	Remote Similarity	NPD5330	Approved
0.6579	Remote Similarity	NPD6684	Approved
0.6579	Remote Similarity	NPD7334	Approved
0.6579	Remote Similarity	NPD6409	Approved
0.6579	Remote Similarity	NPD7146	Approved
0.6579	Remote Similarity	NPD7521	Approved
0.6567	Remote Similarity	NPD7604	Phase 2
0.6562	Remote Similarity	NPD6053	Discontinued
0.6535	Remote Similarity	NPD6420	Discontinued
0.6522	Remote Similarity	NPD7751	Phase 1
0.6518	Remote Similarity	NPD3667	Approved
0.6508	Remote Similarity	NPD6881	Approved
0.6508	Remote Similarity	NPD6899	Approved
0.6484	Remote Similarity	NPD6649	Approved
0.6484	Remote Similarity	NPD6650	Approved
0.6466	Remote Similarity	NPD6672	Approved
0.6466	Remote Similarity	NPD5737	Approved
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7122	Discontinued
0.6441	Remote Similarity	NPD7637	Suspended
0.6435	Remote Similarity	NPD3618	Phase 1
0.6434	Remote Similarity	NPD6333	Approved
0.6434	Remote Similarity	NPD6334	Approved
0.6429	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD5697	Approved
0.6417	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7102	Approved
0.6406	Remote Similarity	NPD6883	Approved
0.6406	Remote Similarity	NPD7290	Approved
0.6404	Remote Similarity	NPD3666	Approved
0.6404	Remote Similarity	NPD3133	Approved
0.6404	Remote Similarity	NPD3665	Phase 1
0.6397	Remote Similarity	NPD7492	Approved
0.6393	Remote Similarity	NPD5696	Approved
0.6387	Remote Similarity	NPD5779	Approved
0.6387	Remote Similarity	NPD5778	Approved
0.6385	Remote Similarity	NPD4632	Approved
0.6378	Remote Similarity	NPD6011	Approved
0.6377	Remote Similarity	NPD8337	Approved
0.6377	Remote Similarity	NPD8336	Approved
0.6371	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD4697	Phase 3
0.6357	Remote Similarity	NPD8130	Phase 1
0.6357	Remote Similarity	NPD6869	Approved
0.6357	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6617	Approved
0.6357	Remote Similarity	NPD6847	Approved
0.635	Remote Similarity	NPD7507	Approved
0.635	Remote Similarity	NPD6616	Approved
0.6348	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6054	Approved
0.6343	Remote Similarity	NPD6059	Approved
0.6341	Remote Similarity	NPD8418	Phase 2
0.6333	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6014	Approved
0.6328	Remote Similarity	NPD6013	Approved
0.6328	Remote Similarity	NPD6012	Approved
0.6308	Remote Similarity	NPD7336	Phase 2
0.6308	Remote Similarity	NPD7335	Phase 2
0.6308	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8297	Approved
0.6308	Remote Similarity	NPD6882	Approved
0.6304	Remote Similarity	NPD7078	Approved
0.6304	Remote Similarity	NPD8293	Discontinued
0.6303	Remote Similarity	NPD8034	Phase 2
0.6303	Remote Similarity	NPD8035	Phase 2
0.6299	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD6921	Approved
0.6293	Remote Similarity	NPD6098	Approved
0.6281	Remote Similarity	NPD5695	Phase 3
0.6259	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD6370	Approved
0.6241	Remote Similarity	NPD6009	Approved
0.624	Remote Similarity	NPD5211	Phase 2
0.623	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5222	Approved
0.623	Remote Similarity	NPD5221	Approved
0.6222	Remote Similarity	NPD6319	Approved
0.6218	Remote Similarity	NPD5207	Approved
0.6214	Remote Similarity	NPD7319	Approved
0.6198	Remote Similarity	NPD7748	Approved
0.6198	Remote Similarity	NPD6001	Approved
0.6179	Remote Similarity	NPD7902	Approved
0.6179	Remote Similarity	NPD5173	Approved
0.6179	Remote Similarity	NPD4755	Approved
0.6176	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5983	Phase 2
0.6176	Remote Similarity	NPD6016	Approved
0.6176	Remote Similarity	NPD6015	Approved
0.6174	Remote Similarity	NPD5362	Discontinued
0.6167	Remote Similarity	NPD6411	Approved
0.6167	Remote Similarity	NPD7515	Phase 2
0.6165	Remote Similarity	NPD6868	Approved
0.6161	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD8342	Approved
0.6159	Remote Similarity	NPD8340	Approved
0.6159	Remote Similarity	NPD8341	Approved
0.6159	Remote Similarity	NPD8299	Approved
0.6154	Remote Similarity	NPD5279	Phase 3
0.6142	Remote Similarity	NPD5141	Approved
0.614	Remote Similarity	NPD857	Phase 3
0.6134	Remote Similarity	NPD6051	Approved
0.6134	Remote Similarity	NPD4753	Phase 2
0.6134	Remote Similarity	NPD6673	Approved
0.6134	Remote Similarity	NPD6904	Approved
0.6134	Remote Similarity	NPD6080	Approved
0.6131	Remote Similarity	NPD5988	Approved
0.6116	Remote Similarity	NPD4202	Approved
0.6115	Remote Similarity	NPD6336	Discontinued
0.6102	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7839	Suspended
0.6087	Remote Similarity	NPD4223	Phase 3
0.6087	Remote Similarity	NPD4221	Approved
0.608	Remote Similarity	NPD4700	Approved
0.608	Remote Similarity	NPD5285	Approved
0.608	Remote Similarity	NPD5286	Approved
0.608	Remote Similarity	NPD4696	Approved
0.6074	Remote Similarity	NPD6335	Approved
0.6069	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5329	Approved
0.6066	Remote Similarity	NPD5771	Approved
0.605	Remote Similarity	NPD5208	Approved
0.6045	Remote Similarity	NPD7754	Approved
0.6045	Remote Similarity	NPD6274	Approved
0.6045	Remote Similarity	NPD7755	Approved
0.6036	Remote Similarity	NPD7339	Approved
0.6036	Remote Similarity	NPD6942	Approved
0.6034	Remote Similarity	NPD6695	Phase 3
0.6033	Remote Similarity	NPD5284	Approved
0.6033	Remote Similarity	NPD5693	Phase 1
0.6033	Remote Similarity	NPD5281	Approved
0.6032	Remote Similarity	NPD5223	Approved
0.6031	Remote Similarity	NPD6421	Discontinued
0.6029	Remote Similarity	NPD7101	Approved
0.6029	Remote Similarity	NPD7100	Approved
0.6028	Remote Similarity	NPD6033	Approved
0.6017	Remote Similarity	NPD5786	Approved
0.6017	Remote Similarity	NPD8308	Discontinued
0.6016	Remote Similarity	NPD4629	Approved
0.6016	Remote Similarity	NPD5210	Approved
0.6015	Remote Similarity	NPD8298	Phase 2
0.6	Remote Similarity	NPD6101	Approved
0.6	Remote Similarity	NPD4225	Approved
0.6	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD5225	Approved
0.5984	Remote Similarity	NPD4633	Approved
0.5984	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD5226	Approved
0.5983	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD3668	Phase 3
0.5983	Remote Similarity	NPD4197	Approved
0.5972	Remote Similarity	NPD8338	Approved
0.5971	Remote Similarity	NPD7829	Approved
0.5971	Remote Similarity	NPD7830	Approved
0.5969	Remote Similarity	NPD6920	Discontinued
0.5966	Remote Similarity	NPD4251	Approved
0.5966	Remote Similarity	NPD4250	Approved
0.5965	Remote Similarity	NPD6929	Approved
0.5957	Remote Similarity	NPD8448	Approved
0.5957	Remote Similarity	NPD8074	Phase 3
0.5956	Remote Similarity	NPD6313	Approved
0.5956	Remote Similarity	NPD7641	Discontinued
0.5956	Remote Similarity	NPD6314	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