NPASS Compound

Structure

NPC157257 OpenBabel07101718182D 35 38 0 0 1 0 0 0 0 0999 V2000 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9792 -6.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4743 -6.2722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 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 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 7 31 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 28 1 0 0 0 0 17 32 1 0 0 0 0 18 19 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 21 1 1 1 0 0 0 21 22 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 29 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 1 0 0 0 26 29 1 0 0 0 0 26 33 1 1 0 0 0 27 30 1 6 0 0 0 27 32 1 0 0 0 0 28 35 1 0 0 0 0 30 6 1 1 0 0 0 31 32 1 1 0 0 0 32 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.41
Volume:	548.9
LogP:	7.616
LogD:	5.476
LogS:	-6.405
# Rotatable Bonds:	6
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	5.2
Fsp3:	0.875
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:	-4.81
MDCK Permeability:	1.3596858480013907e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	96.82209014892578%
Volume Distribution (VD):	1.801
Pgp-substrate:	4.166484832763672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.365
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.251
CYP2D6-substrate:	0.621
CYP3A4-inhibitor:	0.778
CYP3A4-substrate:	0.807

ADMET: Excretion

Clearance (CL):	4.671
Half-life (T1/2):	0.046

ADMET: Toxicity

hERG Blockers:	0.581
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.251
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.215
Carcinogencity:	0.048
Eye Corrosion:	0.004
Eye Irritation:	0.009
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC157257

Natural Product ID:	NPC157257
*Common Name:**	3Beta-Hydroxy-7Beta,25-Dimethoxycucurbita-5,23(E)-Diene
IUPAC Name:	(3S,7S,8R,9S,10S,13R,14S,17R)-7-methoxy-17-[(E,2R)-6-methoxy-6-methylhept-4-en-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	OJXKMMLNVLFMJM-QTACYZFBSA-N
Standard InCHI:	InChI=1S/C32H54O3/c1-21(12-11-16-28(2,3)35-10)22-15-17-32(8)27-25(34-9)20-24-23(13-14-26(33)29(24,4)5)30(27,6)18-19-31(22,32)7/h11,16,20-23,25-27,33H,12-15,17-19H2,1-10H3/b16-11+/t21-,22-,23-,25+,26+,27-,30+,31-,32+/m1/s1
SMILES:	C[C@H](C/C=C/C(C)(C)OC)[C@H]1CC[C@@]2(C)[C@@H]3[C@H](C=C4[C@@H](CC[C@@H](C4(C)C)O)[C@]3(C)CC[C@]12C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469190
PubChem CID:	16079963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17685651]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[18637688]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24836069]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621938]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Vines	n.a.	n.a.	PMID[32357011]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8182	Momordica charantia	Species	Cucurbitaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1086	Cell Line	SK-HEP1	Homo sapiens	IC50	>	100000.0	nM	PMID[554317]

☑ 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 NPC157257 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	167
0.1-0.2	1294
0.2-0.3	4773
0.3-0.4	14976
0.4-0.5	8812
0.5-0.6	6321
0.6-0.7	4729
0.7-0.8	1346
0.8-0.85	148
0.85-0.9	98
0.9-0.95	23
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC274448
0.9625	High Similarity	NPC470077
0.9512	High Similarity	NPC149224
0.9494	High Similarity	NPC82986
0.9494	High Similarity	NPC7505
0.9494	High Similarity	NPC474683
0.9494	High Similarity	NPC474759
0.9494	High Similarity	NPC474752
0.9494	High Similarity	NPC474731
0.9375	High Similarity	NPC49964
0.9375	High Similarity	NPC470049
0.9268	High Similarity	NPC266511
0.9259	High Similarity	NPC470558
0.925	High Similarity	NPC264245
0.925	High Similarity	NPC47761
0.9176	High Similarity	NPC295668
0.9146	High Similarity	NPC205845
0.9125	High Similarity	NPC234193
0.9125	High Similarity	NPC241290
0.9125	High Similarity	NPC209944
0.9125	High Similarity	NPC164840
0.9024	High Similarity	NPC475789
0.9	High Similarity	NPC28862
0.9	High Similarity	NPC47982
0.9	High Similarity	NPC109546
0.9	High Similarity	NPC81306
0.9	High Similarity	NPC84694
0.9	High Similarity	NPC143182
0.8987	High Similarity	NPC155986
0.8987	High Similarity	NPC198968
0.8987	High Similarity	NPC318495
0.8929	High Similarity	NPC261266
0.8902	High Similarity	NPC296701
0.8902	High Similarity	NPC87489
0.8902	High Similarity	NPC50964
0.8902	High Similarity	NPC218616
0.8902	High Similarity	NPC101462
0.8876	High Similarity	NPC98457
0.8876	High Similarity	NPC227583
0.8876	High Similarity	NPC12103
0.8875	High Similarity	NPC473943
0.8875	High Similarity	NPC474216
0.8864	High Similarity	NPC127718
0.8864	High Similarity	NPC65402
0.8861	High Similarity	NPC321016
0.8861	High Similarity	NPC240604
0.8861	High Similarity	NPC300324
0.8861	High Similarity	NPC113733
0.8861	High Similarity	NPC321381
0.8861	High Similarity	NPC107059
0.8851	High Similarity	NPC177641
0.881	High Similarity	NPC318390
0.8795	High Similarity	NPC474634
0.878	High Similarity	NPC23852
0.878	High Similarity	NPC209620
0.8778	High Similarity	NPC291634
0.8765	High Similarity	NPC209430
0.8765	High Similarity	NPC30986
0.8765	High Similarity	NPC328714
0.8764	High Similarity	NPC8774
0.8734	High Similarity	NPC28657
0.8734	High Similarity	NPC304309
0.8734	High Similarity	NPC162742
0.8734	High Similarity	NPC134847
0.8734	High Similarity	NPC136188
0.8734	High Similarity	NPC288035
0.8734	High Similarity	NPC230301
0.8734	High Similarity	NPC285893
0.8734	High Similarity	NPC22105
0.8721	High Similarity	NPC471952
0.8706	High Similarity	NPC6391
0.869	High Similarity	NPC185568
0.869	High Similarity	NPC474047
0.869	High Similarity	NPC238485
0.869	High Similarity	NPC231310
0.8675	High Similarity	NPC189972
0.8667	High Similarity	NPC288970
0.8652	High Similarity	NPC144202
0.8642	High Similarity	NPC285761
0.8642	High Similarity	NPC76931
0.8642	High Similarity	NPC275910
0.8642	High Similarity	NPC87604
0.8642	High Similarity	NPC477522
0.8642	High Similarity	NPC18603
0.8642	High Similarity	NPC307965
0.8625	High Similarity	NPC247325
0.8625	High Similarity	NPC134330
0.8625	High Similarity	NPC129165
0.8625	High Similarity	NPC244488
0.8625	High Similarity	NPC189883
0.8588	High Similarity	NPC470360
0.8571	High Similarity	NPC126815
0.8571	High Similarity	NPC134481
0.8571	High Similarity	NPC317458
0.8571	High Similarity	NPC82623
0.8554	High Similarity	NPC474531
0.8554	High Similarity	NPC470383
0.8539	High Similarity	NPC27531
0.8537	High Similarity	NPC1319
0.8537	High Similarity	NPC80530
0.8537	High Similarity	NPC273410
0.8523	High Similarity	NPC3345
0.8523	High Similarity	NPC291484
0.8523	High Similarity	NPC11216
0.8523	High Similarity	NPC329596
0.8523	High Similarity	NPC204188
0.8523	High Similarity	NPC80561
0.8519	High Similarity	NPC214570
0.8519	High Similarity	NPC34019
0.8519	High Similarity	NPC91594
0.8506	High Similarity	NPC133588
0.85	High Similarity	NPC257347
0.85	High Similarity	NPC141071
0.85	High Similarity	NPC471723
0.8488	Intermediate Similarity	NPC299068
0.8488	Intermediate Similarity	NPC293287
0.8488	Intermediate Similarity	NPC152808
0.8481	Intermediate Similarity	NPC471799
0.8462	Intermediate Similarity	NPC78473
0.8452	Intermediate Similarity	NPC30166
0.8452	Intermediate Similarity	NPC304285
0.8452	Intermediate Similarity	NPC202389
0.8452	Intermediate Similarity	NPC5985
0.8452	Intermediate Similarity	NPC155521
0.8434	Intermediate Similarity	NPC322313
0.8434	Intermediate Similarity	NPC236237
0.8434	Intermediate Similarity	NPC13554
0.8434	Intermediate Similarity	NPC236112
0.8434	Intermediate Similarity	NPC26117
0.8434	Intermediate Similarity	NPC102253
0.8427	Intermediate Similarity	NPC471453
0.8427	Intermediate Similarity	NPC234335
0.8427	Intermediate Similarity	NPC41554
0.8427	Intermediate Similarity	NPC97404
0.8415	Intermediate Similarity	NPC477514
0.8415	Intermediate Similarity	NPC244385
0.8415	Intermediate Similarity	NPC6978
0.8415	Intermediate Similarity	NPC83351
0.8415	Intermediate Similarity	NPC138621
0.8415	Intermediate Similarity	NPC167891
0.8415	Intermediate Similarity	NPC167037
0.8409	Intermediate Similarity	NPC470361
0.8395	Intermediate Similarity	NPC96319
0.8395	Intermediate Similarity	NPC470362
0.8395	Intermediate Similarity	NPC73875
0.8395	Intermediate Similarity	NPC46160
0.8395	Intermediate Similarity	NPC265588
0.8395	Intermediate Similarity	NPC237460
0.8395	Intermediate Similarity	NPC202642
0.8387	Intermediate Similarity	NPC473510
0.8375	Intermediate Similarity	NPC477138
0.8375	Intermediate Similarity	NPC471797
0.8375	Intermediate Similarity	NPC243342
0.8372	Intermediate Similarity	NPC474349
0.8372	Intermediate Similarity	NPC474189
0.8372	Intermediate Similarity	NPC477578
0.8353	Intermediate Similarity	NPC470384
0.8333	Intermediate Similarity	NPC476646
0.8333	Intermediate Similarity	NPC307776
0.8315	Intermediate Similarity	NPC14380
0.8315	Intermediate Similarity	NPC245410
0.8315	Intermediate Similarity	NPC470390
0.8315	Intermediate Similarity	NPC192437
0.8315	Intermediate Similarity	NPC270511
0.8295	Intermediate Similarity	NPC474668
0.8293	Intermediate Similarity	NPC470711
0.8293	Intermediate Similarity	NPC470758
0.8293	Intermediate Similarity	NPC471798
0.8276	Intermediate Similarity	NPC94462
0.8276	Intermediate Similarity	NPC474970
0.8276	Intermediate Similarity	NPC125399
0.8272	Intermediate Similarity	NPC121744
0.8272	Intermediate Similarity	NPC118508
0.8272	Intermediate Similarity	NPC291503
0.8272	Intermediate Similarity	NPC322353
0.8261	Intermediate Similarity	NPC72204
0.8256	Intermediate Similarity	NPC474493
0.8256	Intermediate Similarity	NPC124172
0.8256	Intermediate Similarity	NPC15534
0.8256	Intermediate Similarity	NPC209802
0.8256	Intermediate Similarity	NPC33913
0.825	Intermediate Similarity	NPC474140
0.825	Intermediate Similarity	NPC182717
0.8242	Intermediate Similarity	NPC292793
0.8235	Intermediate Similarity	NPC470614
0.8235	Intermediate Similarity	NPC201852
0.8235	Intermediate Similarity	NPC1272
0.8235	Intermediate Similarity	NPC248886
0.8235	Intermediate Similarity	NPC471408
0.8228	Intermediate Similarity	NPC475728
0.8214	Intermediate Similarity	NPC96362
0.8202	Intermediate Similarity	NPC146554
0.8202	Intermediate Similarity	NPC473647
0.8202	Intermediate Similarity	NPC101886
0.8193	Intermediate Similarity	NPC11908
0.8193	Intermediate Similarity	NPC476314
0.8193	Intermediate Similarity	NPC85346
0.8193	Intermediate Similarity	NPC65897
0.8193	Intermediate Similarity	NPC205455
0.8193	Intermediate Similarity	NPC186191

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 NPC157257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1403
0.2-0.3	4062
0.3-0.4	2428
0.4-0.5	638
0.5-0.6	195
0.6-0.7	174
0.7-0.8	78
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8734	High Similarity	NPD7339	Approved
0.8734	High Similarity	NPD6942	Approved
0.8434	Intermediate Similarity	NPD7525	Registered
0.8395	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6924	Approved
0.8148	Intermediate Similarity	NPD4784	Approved
0.8148	Intermediate Similarity	NPD4785	Approved
0.8148	Intermediate Similarity	NPD6926	Approved
0.8046	Intermediate Similarity	NPD4786	Approved
0.7952	Intermediate Similarity	NPD6933	Approved
0.7901	Intermediate Similarity	NPD4243	Approved
0.7901	Intermediate Similarity	NPD7150	Approved
0.7901	Intermediate Similarity	NPD7151	Approved
0.7901	Intermediate Similarity	NPD7152	Approved
0.7882	Intermediate Similarity	NPD7645	Phase 2
0.7816	Intermediate Similarity	NPD3667	Approved
0.7791	Intermediate Similarity	NPD6930	Phase 2
0.7791	Intermediate Similarity	NPD6931	Approved
0.7791	Intermediate Similarity	NPD7514	Phase 3
0.7778	Intermediate Similarity	NPD7143	Approved
0.7778	Intermediate Similarity	NPD7144	Approved
0.7765	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6695	Phase 3
0.7674	Intermediate Similarity	NPD6929	Approved
0.7654	Intermediate Similarity	NPD6922	Approved
0.7654	Intermediate Similarity	NPD6923	Approved
0.7647	Intermediate Similarity	NPD6932	Approved
0.764	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6079	Approved
0.7619	Intermediate Similarity	NPD8264	Approved
0.7609	Intermediate Similarity	NPD6051	Approved
0.7609	Intermediate Similarity	NPD5328	Approved
0.7586	Intermediate Similarity	NPD4748	Discontinued
0.7586	Intermediate Similarity	NPD7332	Phase 2
0.7582	Intermediate Similarity	NPD7750	Discontinued
0.7558	Intermediate Similarity	NPD7145	Approved
0.7526	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6902	Approved
0.7473	Intermediate Similarity	NPD3618	Phase 1
0.7471	Intermediate Similarity	NPD4195	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7639	Approved
0.7442	Intermediate Similarity	NPD5776	Phase 2
0.7442	Intermediate Similarity	NPD6925	Approved
0.7412	Intermediate Similarity	NPD5275	Approved
0.7412	Intermediate Similarity	NPD4190	Phase 3
0.7391	Intermediate Similarity	NPD7524	Approved
0.7386	Intermediate Similarity	NPD7509	Discontinued
0.7368	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD4202	Approved
0.7363	Intermediate Similarity	NPD6893	Approved
0.7273	Intermediate Similarity	NPD6683	Phase 2
0.7253	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD3133	Approved
0.7253	Intermediate Similarity	NPD3665	Phase 1
0.7222	Intermediate Similarity	NPD7115	Discovery
0.72	Intermediate Similarity	NPD4159	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5211	Phase 2
0.7111	Intermediate Similarity	NPD6898	Phase 1
0.71	Intermediate Similarity	NPD5286	Approved
0.71	Intermediate Similarity	NPD4696	Approved
0.71	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD7087	Discontinued
0.7071	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD5173	Approved
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7053	Intermediate Similarity	NPD4753	Phase 2
0.7033	Intermediate Similarity	NPD4223	Phase 3
0.7033	Intermediate Similarity	NPD4221	Approved
0.703	Intermediate Similarity	NPD5223	Approved
0.699	Remote Similarity	NPD5141	Approved
0.6989	Remote Similarity	NPD5329	Approved
0.6989	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4697	Phase 3
0.6961	Remote Similarity	NPD5224	Approved
0.6961	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD4633	Approved
0.6961	Remote Similarity	NPD5225	Approved
0.6952	Remote Similarity	NPD6881	Approved
0.6952	Remote Similarity	NPD6899	Approved
0.6931	Remote Similarity	NPD4700	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6915	Remote Similarity	NPD5279	Phase 3
0.6907	Remote Similarity	NPD7637	Suspended
0.69	Remote Similarity	NPD6084	Phase 2
0.69	Remote Similarity	NPD6083	Phase 2
0.6893	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD5175	Approved
0.6882	Remote Similarity	NPD4197	Approved
0.6869	Remote Similarity	NPD5210	Approved
0.6869	Remote Similarity	NPD4629	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6832	Remote Similarity	NPD4225	Approved
0.6832	Remote Similarity	NPD5290	Discontinued
0.6824	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7290	Approved
0.6822	Remote Similarity	NPD6883	Approved
0.6822	Remote Similarity	NPD7102	Approved
0.6814	Remote Similarity	NPD8033	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6792	Remote Similarity	NPD6011	Approved
0.6792	Remote Similarity	NPD7320	Approved
0.679	Remote Similarity	NPD368	Approved
0.6774	Remote Similarity	NPD4788	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6759	Remote Similarity	NPD6617	Approved
0.6759	Remote Similarity	NPD6869	Approved
0.6759	Remote Similarity	NPD6649	Approved
0.6759	Remote Similarity	NPD6847	Approved
0.6759	Remote Similarity	NPD6650	Approved
0.6737	Remote Similarity	NPD4693	Phase 3
0.6737	Remote Similarity	NPD6409	Approved
0.6737	Remote Similarity	NPD4688	Approved
0.6737	Remote Similarity	NPD4138	Approved
0.6737	Remote Similarity	NPD5330	Approved
0.6737	Remote Similarity	NPD7521	Approved
0.6737	Remote Similarity	NPD6684	Approved
0.6737	Remote Similarity	NPD5690	Phase 2
0.6737	Remote Similarity	NPD4689	Approved
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4690	Approved
0.6737	Remote Similarity	NPD5205	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6737	Remote Similarity	NPD7334	Approved
0.6737	Remote Similarity	NPD7146	Approved
0.6735	Remote Similarity	NPD8034	Phase 2
0.6735	Remote Similarity	NPD8035	Phase 2
0.6735	Remote Similarity	NPD7515	Phase 2
0.6731	Remote Similarity	NPD4754	Approved
0.6729	Remote Similarity	NPD6373	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6372	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6726	Remote Similarity	NPD8377	Approved
0.6726	Remote Similarity	NPD8294	Approved
0.6698	Remote Similarity	NPD5701	Approved
0.6697	Remote Similarity	NPD6882	Approved
0.6696	Remote Similarity	NPD7327	Approved
0.6696	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6637	Remote Similarity	NPD7516	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6606	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4768	Approved
0.6604	Remote Similarity	NPD4767	Approved
0.6598	Remote Similarity	NPD4723	Approved
0.6598	Remote Similarity	NPD6903	Approved
0.6598	Remote Similarity	NPD5737	Approved
0.6598	Remote Similarity	NPD6672	Approved
0.6598	Remote Similarity	NPD4722	Approved
0.6598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7741	Discontinued
0.6569	Remote Similarity	NPD7902	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6562	Remote Similarity	NPD6098	Approved
0.6562	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5280	Approved
0.6562	Remote Similarity	NPD4694	Approved
0.6552	Remote Similarity	NPD4787	Phase 1
0.6535	Remote Similarity	NPD5695	Phase 3
0.6514	Remote Similarity	NPD5135	Approved
0.6514	Remote Similarity	NPD5249	Phase 3
0.6514	Remote Similarity	NPD5250	Approved
0.6514	Remote Similarity	NPD4634	Approved
0.6514	Remote Similarity	NPD5169	Approved
0.6514	Remote Similarity	NPD5248	Approved
0.6514	Remote Similarity	NPD5247	Approved
0.6514	Remote Similarity	NPD5251	Approved
0.6514	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5696	Approved
0.6486	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD5168	Approved
0.6481	Remote Similarity	NPD5128	Approved
0.6465	Remote Similarity	NPD7136	Phase 2
0.6455	Remote Similarity	NPD5217	Approved
0.6455	Remote Similarity	NPD5216	Approved
0.6455	Remote Similarity	NPD5215	Approved
0.6455	Remote Similarity	NPD5127	Approved
0.6421	Remote Similarity	NPD5362	Discontinued
0.6413	Remote Similarity	NPD3617	Approved
0.6413	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6335	Approved
0.64	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD5284	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