NPASS Compound

Structure

NPC243985 OpenBabel07101718332D 29 33 0 0 1 0 0 0 0 0999 V2000 -1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 -0.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7734 0.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8253 1.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 2.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0193 2.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8253 -1.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2272 -0.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 -1.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3612 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -0.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8253 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -1.2670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0932 1.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2272 1.7330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0932 0.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 -0.2670 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3612 1.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5573 -1.7670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 10 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 2 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 6 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 29 1 1 0 0 0 21 7 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 24 26 1 1 0 0 0 25 28 2 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	397.33
Volume:	447.28
LogP:	6.536
LogD:	5.013
LogS:	-5.929
# Rotatable Bonds:	2
TPSA:	32.59
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	4.824
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.735
MDCK Permeability:	1.1587038898142055e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.593
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.409
Plasma Protein Binding (PPB):	95.56610870361328%
Volume Distribution (VD):	1.221
Pgp-substrate:	1.8782923221588135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.213
CYP1A2-substrate:	0.313
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.411
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.558
CYP2D6-substrate:	0.711
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	10.698
Half-life (T1/2):	0.025

ADMET: Toxicity

hERG Blockers:	0.831
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.547
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.948
Carcinogencity:	0.87
Eye Corrosion:	0.01
Eye Irritation:	0.04
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC243985

Natural Product ID:	NPC243985
*Common Name:**	[(3S,20R,25S)-22,26-Iminocholesta-5,22(N)-Dien-3-Ol
IUPAC Name:	(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(1R)-1-[(3S)-3-methyl-2,3,4,5-tetrahydropyridin-6-yl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	20-epi-verazine
Standard InCHIKey:	VRBNGKPRTHBEIQ-RWWNDWOOSA-N
Standard InCHI:	InChI=1S/C27H43NO/c1-17-5-10-25(28-16-17)18(2)22-8-9-23-21-7-6-19-15-20(29)11-13-26(19,3)24(21)12-14-27(22,23)4/h6,17-18,20-24,29H,5,7-16H2,1-4H3/t17-,18+,20-,21-,22+,23-,24-,26-,27+/m0/s1
SMILES:	C[C@H]1CCC(=NC1)[C@@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458682
PubChem CID:	44584077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002732] 22,26-epiminocholestanes

*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
NPO33146	eclipta alba	Species	n.a.	Eukaryota	n.a.	suriname rainforest1	n.a.	PMID[9784152]

☑ 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
MIC	2
Others	3

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	0.88	ug ml-1	PMID[469442]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	1.12	ug ml-1	PMID[469442]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	0.69	ug ml-1	PMID[469442]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	6.25	ug.mL-1	PMID[469442]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	12.5	ug.mL-1	PMID[469442]

☑ 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 NPC243985 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	89
0.1-0.2	809
0.2-0.3	9744
0.3-0.4	16626
0.4-0.5	8442
0.5-0.6	5565
0.6-0.7	1225
0.7-0.8	186
0.8-0.85	6
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280710
0.9667	High Similarity	NPC240650
0.9158	High Similarity	NPC293299
0.9158	High Similarity	NPC45365
0.8283	Intermediate Similarity	NPC50815
0.8202	Intermediate Similarity	NPC192456
0.82	Intermediate Similarity	NPC474583
0.81	Intermediate Similarity	NPC247060
0.8061	Intermediate Similarity	NPC474164
0.8043	Intermediate Similarity	NPC75810
0.798	Intermediate Similarity	NPC91604
0.7961	Intermediate Similarity	NPC25340
0.7931	Intermediate Similarity	NPC134847
0.7931	Intermediate Similarity	NPC285893
0.7931	Intermediate Similarity	NPC304309
0.7931	Intermediate Similarity	NPC288035
0.7931	Intermediate Similarity	NPC28657
0.7931	Intermediate Similarity	NPC22105
0.7931	Intermediate Similarity	NPC136188
0.7931	Intermediate Similarity	NPC230301
0.7931	Intermediate Similarity	NPC162742
0.7921	Intermediate Similarity	NPC471083
0.7841	Intermediate Similarity	NPC240604
0.7841	Intermediate Similarity	NPC300324
0.7841	Intermediate Similarity	NPC107059
0.7841	Intermediate Similarity	NPC113733
0.7841	Intermediate Similarity	NPC321381
0.7841	Intermediate Similarity	NPC321016
0.7778	Intermediate Similarity	NPC476903
0.7753	Intermediate Similarity	NPC34019
0.7753	Intermediate Similarity	NPC198968
0.7753	Intermediate Similarity	NPC155986
0.7753	Intermediate Similarity	NPC318495
0.7745	Intermediate Similarity	NPC176012
0.7727	Intermediate Similarity	NPC257347
0.7727	Intermediate Similarity	NPC141071
0.7727	Intermediate Similarity	NPC471723
0.7717	Intermediate Similarity	NPC5985
0.77	Intermediate Similarity	NPC140300
0.7667	Intermediate Similarity	NPC76931
0.7667	Intermediate Similarity	NPC87604
0.7667	Intermediate Similarity	NPC18603
0.7667	Intermediate Similarity	NPC307965
0.7667	Intermediate Similarity	NPC474216
0.7667	Intermediate Similarity	NPC473943
0.7667	Intermediate Similarity	NPC477522
0.764	Intermediate Similarity	NPC134330
0.764	Intermediate Similarity	NPC189883
0.764	Intermediate Similarity	NPC129165
0.7619	Intermediate Similarity	NPC169375
0.7604	Intermediate Similarity	NPC34754
0.7596	Intermediate Similarity	NPC212874
0.7593	Intermediate Similarity	NPC56796
0.7582	Intermediate Similarity	NPC47982
0.7582	Intermediate Similarity	NPC328714
0.7582	Intermediate Similarity	NPC81306
0.7582	Intermediate Similarity	NPC109546
0.7582	Intermediate Similarity	NPC84694
0.7582	Intermediate Similarity	NPC143182
0.7582	Intermediate Similarity	NPC28862
0.7526	Intermediate Similarity	NPC249312
0.75	Intermediate Similarity	NPC234193
0.75	Intermediate Similarity	NPC164840
0.75	Intermediate Similarity	NPC26117
0.75	Intermediate Similarity	NPC209944
0.75	Intermediate Similarity	NPC241290
0.7473	Intermediate Similarity	NPC275910
0.7453	Intermediate Similarity	NPC46981
0.7449	Intermediate Similarity	NPC84171
0.7447	Intermediate Similarity	NPC246956
0.7444	Intermediate Similarity	NPC237460
0.7444	Intermediate Similarity	NPC244488
0.7444	Intermediate Similarity	NPC470362
0.7444	Intermediate Similarity	NPC247325
0.7444	Intermediate Similarity	NPC202642
0.7444	Intermediate Similarity	NPC46160
0.7444	Intermediate Similarity	NPC96319
0.7429	Intermediate Similarity	NPC119329
0.7426	Intermediate Similarity	NPC289140
0.7419	Intermediate Similarity	NPC474531
0.7419	Intermediate Similarity	NPC474752
0.7419	Intermediate Similarity	NPC82986
0.7419	Intermediate Similarity	NPC474759
0.7419	Intermediate Similarity	NPC7505
0.7419	Intermediate Similarity	NPC474683
0.7419	Intermediate Similarity	NPC209620
0.7419	Intermediate Similarity	NPC474731
0.7419	Intermediate Similarity	NPC264245
0.7419	Intermediate Similarity	NPC470383
0.7419	Intermediate Similarity	NPC23852
0.7419	Intermediate Similarity	NPC47761
0.7391	Intermediate Similarity	NPC30986
0.7391	Intermediate Similarity	NPC1319
0.7391	Intermediate Similarity	NPC209430
0.7383	Intermediate Similarity	NPC159367
0.7379	Intermediate Similarity	NPC275686
0.7368	Intermediate Similarity	NPC209802
0.7363	Intermediate Similarity	NPC214570
0.7358	Intermediate Similarity	NPC55462
0.734	Intermediate Similarity	NPC49964
0.734	Intermediate Similarity	NPC189972
0.734	Intermediate Similarity	NPC50964
0.734	Intermediate Similarity	NPC1272
0.734	Intermediate Similarity	NPC470614
0.734	Intermediate Similarity	NPC101462
0.734	Intermediate Similarity	NPC248886
0.7333	Intermediate Similarity	NPC322353
0.7333	Intermediate Similarity	NPC118508
0.7333	Intermediate Similarity	NPC121744
0.7327	Intermediate Similarity	NPC311164
0.7327	Intermediate Similarity	NPC272732
0.7315	Intermediate Similarity	NPC95920
0.7315	Intermediate Similarity	NPC85001
0.7315	Intermediate Similarity	NPC253645
0.7315	Intermediate Similarity	NPC147835
0.7312	Intermediate Similarity	NPC236112
0.7303	Intermediate Similarity	NPC471799
0.7303	Intermediate Similarity	NPC474140
0.73	Intermediate Similarity	NPC93027
0.7283	Intermediate Similarity	NPC244385
0.7283	Intermediate Similarity	NPC477514
0.7283	Intermediate Similarity	NPC6978
0.7283	Intermediate Similarity	NPC167037
0.7283	Intermediate Similarity	NPC285761
0.7283	Intermediate Similarity	NPC186191
0.7283	Intermediate Similarity	NPC205455
0.7283	Intermediate Similarity	NPC302041
0.7283	Intermediate Similarity	NPC65897
0.7283	Intermediate Similarity	NPC138621
0.7283	Intermediate Similarity	NPC85346
0.7263	Intermediate Similarity	NPC317458
0.7263	Intermediate Similarity	NPC474634
0.7263	Intermediate Similarity	NPC475789
0.7253	Intermediate Similarity	NPC106364
0.7253	Intermediate Similarity	NPC73875
0.7248	Intermediate Similarity	NPC472359
0.7241	Intermediate Similarity	NPC208999
0.7241	Intermediate Similarity	NPC160209
0.7222	Intermediate Similarity	NPC471797
0.7222	Intermediate Similarity	NPC469593
0.7222	Intermediate Similarity	NPC100334
0.7222	Intermediate Similarity	NPC469534
0.7222	Intermediate Similarity	NPC469533
0.7216	Intermediate Similarity	NPC24277
0.7212	Intermediate Similarity	NPC135799
0.7204	Intermediate Similarity	NPC273410
0.7204	Intermediate Similarity	NPC80530
0.7196	Intermediate Similarity	NPC258130
0.7188	Intermediate Similarity	NPC185568
0.7188	Intermediate Similarity	NPC472265
0.7188	Intermediate Similarity	NPC124172
0.7188	Intermediate Similarity	NPC59453
0.7188	Intermediate Similarity	NPC205845
0.7188	Intermediate Similarity	NPC33913
0.7188	Intermediate Similarity	NPC221758
0.717	Intermediate Similarity	NPC241879
0.7158	Intermediate Similarity	NPC470049
0.7158	Intermediate Similarity	NPC30166
0.7158	Intermediate Similarity	NPC201852
0.7158	Intermediate Similarity	NPC20853
0.7143	Intermediate Similarity	NPC471468
0.7128	Intermediate Similarity	NPC236237
0.7128	Intermediate Similarity	NPC102253
0.7128	Intermediate Similarity	NPC13554
0.7128	Intermediate Similarity	NPC322313
0.7113	Intermediate Similarity	NPC474349
0.7113	Intermediate Similarity	NPC474189
0.7113	Intermediate Similarity	NPC266511
0.7113	Intermediate Similarity	NPC274448
0.7113	Intermediate Similarity	NPC157257
0.7111	Intermediate Similarity	NPC201373
0.7111	Intermediate Similarity	NPC182717
0.7097	Intermediate Similarity	NPC318136
0.7097	Intermediate Similarity	NPC22955
0.7097	Intermediate Similarity	NPC312328
0.7097	Intermediate Similarity	NPC470396
0.7097	Intermediate Similarity	NPC474989
0.7097	Intermediate Similarity	NPC99168
0.7091	Intermediate Similarity	NPC328052
0.7079	Intermediate Similarity	NPC475728
0.7079	Intermediate Similarity	NPC145498
0.7071	Intermediate Similarity	NPC316186
0.7071	Intermediate Similarity	NPC470542
0.7065	Intermediate Similarity	NPC122418
0.7065	Intermediate Similarity	NPC265328
0.7065	Intermediate Similarity	NPC30590
0.7065	Intermediate Similarity	NPC290598
0.7065	Intermediate Similarity	NPC27765
0.7065	Intermediate Similarity	NPC120098
0.7059	Intermediate Similarity	NPC473314
0.7054	Intermediate Similarity	NPC478137
0.7041	Intermediate Similarity	NPC293287
0.7041	Intermediate Similarity	NPC31564
0.7041	Intermediate Similarity	NPC6391
0.7041	Intermediate Similarity	NPC474778
0.7041	Intermediate Similarity	NPC152808
0.7041	Intermediate Similarity	NPC94462
0.7041	Intermediate Similarity	NPC474970
0.7041	Intermediate Similarity	NPC145879
0.7041	Intermediate Similarity	NPC474732

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 NPC243985 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	475
0.2-0.3	3390
0.3-0.4	3927
0.4-0.5	883
0.5-0.6	272
0.6-0.7	87
0.7-0.8	19
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
0.7931	Intermediate Similarity	NPD7339	Approved
0.7931	Intermediate Similarity	NPD6942	Approved
0.7576	Intermediate Similarity	NPD5771	Approved
0.7444	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4722	Approved
0.7245	Intermediate Similarity	NPD4723	Approved
0.7188	Intermediate Similarity	NPD4786	Approved
0.7128	Intermediate Similarity	NPD7525	Registered
0.7033	Intermediate Similarity	NPD4784	Approved
0.7033	Intermediate Similarity	NPD6924	Approved
0.7033	Intermediate Similarity	NPD4785	Approved
0.7033	Intermediate Similarity	NPD6926	Approved
0.7	Intermediate Similarity	NPD7151	Approved
0.7	Intermediate Similarity	NPD7150	Approved
0.7	Intermediate Similarity	NPD7152	Approved
0.7	Intermediate Similarity	NPD4243	Approved
0.6979	Remote Similarity	NPD3667	Approved
0.6966	Remote Similarity	NPD6923	Approved
0.6966	Remote Similarity	NPD6922	Approved
0.6889	Remote Similarity	NPD6939	Phase 2
0.6889	Remote Similarity	NPD7143	Approved
0.6889	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7144	Approved
0.6882	Remote Similarity	NPD6933	Approved
0.6882	Remote Similarity	NPD1346	Approved
0.6842	Remote Similarity	NPD7645	Phase 2
0.68	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD6705	Phase 1
0.6602	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6931	Approved
0.6598	Remote Similarity	NPD4748	Discontinued
0.6598	Remote Similarity	NPD6930	Phase 2
0.6596	Remote Similarity	NPD4190	Phase 3
0.6596	Remote Similarity	NPD5275	Approved
0.6574	Remote Similarity	NPD6404	Discontinued
0.6571	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5707	Approved
0.6538	Remote Similarity	NPD6079	Approved
0.6535	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD3133	Approved
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.6476	Remote Similarity	NPD6399	Phase 3
0.6458	Remote Similarity	NPD6925	Approved
0.6458	Remote Similarity	NPD6932	Approved
0.6458	Remote Similarity	NPD5776	Phase 2
0.6429	Remote Similarity	NPD6640	Phase 3
0.6429	Remote Similarity	NPD7509	Discontinued
0.64	Remote Similarity	NPD6695	Phase 3
0.6392	Remote Similarity	NPD7145	Approved
0.6348	Remote Similarity	NPD6420	Discontinued
0.6337	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3668	Phase 3
0.6327	Remote Similarity	NPD6683	Phase 2
0.6327	Remote Similarity	NPD4195	Approved
0.6321	Remote Similarity	NPD4202	Approved
0.6286	Remote Similarity	NPD6700	Approved
0.6286	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7333	Discontinued
0.6275	Remote Similarity	NPD6893	Approved
0.6275	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8418	Phase 2
0.6263	Remote Similarity	NPD7514	Phase 3
0.6237	Remote Similarity	NPD15	Approved
0.6237	Remote Similarity	NPD791	Approved
0.6224	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5279	Phase 3
0.62	Remote Similarity	NPD6902	Approved
0.619	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD7524	Approved
0.6154	Remote Similarity	NPD7750	Discontinued
0.6147	Remote Similarity	NPD5222	Approved
0.6147	Remote Similarity	NPD5221	Approved
0.6147	Remote Similarity	NPD4697	Phase 3
0.6147	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4221	Approved
0.6139	Remote Similarity	NPD4223	Phase 3
0.6124	Remote Similarity	NPD8449	Approved
0.6117	Remote Similarity	NPD5329	Approved
0.61	Remote Similarity	NPD7332	Phase 2
0.6091	Remote Similarity	NPD5173	Approved
0.6091	Remote Similarity	NPD4755	Approved
0.6082	Remote Similarity	NPD8264	Approved
0.6077	Remote Similarity	NPD8450	Suspended
0.6075	Remote Similarity	NPD6702	Approved
0.6075	Remote Similarity	NPD7515	Phase 2
0.6075	Remote Similarity	NPD6703	Approved
0.604	Remote Similarity	NPD6898	Phase 1
0.6019	Remote Similarity	NPD4197	Approved
0.5982	Remote Similarity	NPD5285	Approved
0.5982	Remote Similarity	NPD5286	Approved
0.5982	Remote Similarity	NPD4696	Approved
0.5982	Remote Similarity	NPD4700	Approved
0.5968	Remote Similarity	NPD6909	Approved
0.5968	Remote Similarity	NPD6908	Approved
0.5946	Remote Similarity	NPD6084	Phase 2
0.5946	Remote Similarity	NPD6083	Phase 2
0.5943	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7522	Discontinued
0.5929	Remote Similarity	NPD5223	Approved
0.5929	Remote Similarity	NPD4159	Approved
0.5926	Remote Similarity	NPD7087	Discontinued
0.5922	Remote Similarity	NPD4788	Approved
0.5909	Remote Similarity	NPD5210	Approved
0.5909	Remote Similarity	NPD4629	Approved
0.5905	Remote Similarity	NPD5205	Approved
0.5905	Remote Similarity	NPD4138	Approved
0.5905	Remote Similarity	NPD5330	Approved
0.5905	Remote Similarity	NPD7521	Approved
0.5905	Remote Similarity	NPD6684	Approved
0.5905	Remote Similarity	NPD4693	Phase 3
0.5905	Remote Similarity	NPD6409	Approved
0.5905	Remote Similarity	NPD4688	Approved
0.5905	Remote Similarity	NPD7146	Approved
0.5905	Remote Similarity	NPD4690	Approved
0.5905	Remote Similarity	NPD7334	Approved
0.5905	Remote Similarity	NPD4689	Approved
0.5895	Remote Similarity	NPD1082	Approved
0.5893	Remote Similarity	NPD7638	Approved
0.5893	Remote Similarity	NPD5290	Discontinued
0.5888	Remote Similarity	NPD6051	Approved
0.5877	Remote Similarity	NPD5225	Approved
0.5877	Remote Similarity	NPD4633	Approved
0.5877	Remote Similarity	NPD5211	Phase 2
0.5877	Remote Similarity	NPD5226	Approved
0.5877	Remote Similarity	NPD5224	Approved
0.5872	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7128	Approved
0.5862	Remote Similarity	NPD5357	Phase 1
0.5862	Remote Similarity	NPD6675	Approved
0.5862	Remote Similarity	NPD6402	Approved
0.5862	Remote Similarity	NPD5739	Approved
0.5856	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7639	Approved
0.5841	Remote Similarity	NPD7640	Approved
0.5833	Remote Similarity	NPD4096	Approved
0.5826	Remote Similarity	NPD5174	Approved
0.5826	Remote Similarity	NPD5175	Approved
0.5826	Remote Similarity	NPD4754	Approved
0.5818	Remote Similarity	NPD7748	Approved
0.5794	Remote Similarity	NPD6672	Approved
0.5794	Remote Similarity	NPD5737	Approved
0.5794	Remote Similarity	NPD6903	Approved
0.578	Remote Similarity	NPD8035	Phase 2
0.578	Remote Similarity	NPD8034	Phase 2
0.5778	Remote Similarity	NPD6333	Approved
0.5778	Remote Similarity	NPD6334	Approved
0.5776	Remote Similarity	NPD5141	Approved
0.5772	Remote Similarity	NPD7115	Discovery
0.5763	Remote Similarity	NPD6881	Approved
0.5763	Remote Similarity	NPD8174	Phase 2
0.5763	Remote Similarity	NPD7320	Approved
0.5763	Remote Similarity	NPD6899	Approved
0.5755	Remote Similarity	NPD4694	Approved
0.5755	Remote Similarity	NPD5280	Approved
0.5755	Remote Similarity	NPD5690	Phase 2
0.5743	Remote Similarity	NPD3617	Approved
0.5729	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4768	Approved
0.5726	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD7335	Phase 2
0.5702	Remote Similarity	NPD7336	Phase 2
0.5702	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6412	Phase 2
0.5678	Remote Similarity	NPD5697	Approved
0.5678	Remote Similarity	NPD5701	Approved
0.567	Remote Similarity	NPD4787	Phase 1
0.5667	Remote Similarity	NPD7102	Approved
0.5667	Remote Similarity	NPD7290	Approved
0.5667	Remote Similarity	NPD6883	Approved
0.5664	Remote Similarity	NPD7919	Phase 3
0.5664	Remote Similarity	NPD7920	Phase 3
0.5664	Remote Similarity	NPD7902	Approved
0.5656	Remote Similarity	NPD8298	Phase 2
0.5636	Remote Similarity	NPD7637	Suspended
0.5631	Remote Similarity	NPD4695	Discontinued
0.563	Remote Similarity	NPD4729	Approved
0.563	Remote Similarity	NPD6011	Approved
0.563	Remote Similarity	NPD6406	Approved
0.563	Remote Similarity	NPD5168	Approved
0.563	Remote Similarity	NPD4730	Approved
0.563	Remote Similarity	NPD5128	Approved
0.5625	Remote Similarity	NPD4814	Discontinued
0.5625	Remote Similarity	NPD5695	Phase 3
0.562	Remote Similarity	NPD6617	Approved
0.562	Remote Similarity	NPD6869	Approved
0.562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8130	Phase 1
0.562	Remote Similarity	NPD6650	Approved
0.562	Remote Similarity	NPD6649	Approved
0.562	Remote Similarity	NPD6847	Approved
0.5614	Remote Similarity	NPD5696	Approved
0.5614	Remote Similarity	NPD8088	Phase 1
0.5612	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6098	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