NPASS Compound

Structure

NPC238485 OpenBabel07101718182D 32 35 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 -0.9000 -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 1.7321 2.0000 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 0.8660 1.5000 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 -1.2601 -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 1.5000 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 0.8660 0.5000 0.0000 C 0 0 2 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 -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 -3.1653 -5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 26 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 1 1 1 0 0 0 20 21 1 0 0 0 0 21 29 1 1 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 31 1 1 0 0 0 26 32 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	502.881
LogP:	6.108
LogD:	4.899
LogS:	-5.518
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	5.17
Fsp3:	0.8
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:	-4.814
MDCK Permeability:	8.018352673389018e-06
Pgp-inhibitor:	0.962
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.615
30% Bioavailability (F30%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	96.31148529052734%
Volume Distribution (VD):	1.217
Pgp-substrate:	2.174731731414795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.289
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.295
CYP2D6-inhibitor:	0.799
CYP2D6-substrate:	0.526
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.795

ADMET: Excretion

Clearance (CL):	5.752
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.856
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.942
Carcinogencity:	0.474
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC238485

Natural Product ID:	NPC238485
*Common Name:**	Cucurbita-5(10),6,23(E)-Triene-3Beta,25-Diol
IUPAC Name:	(3S,8S,9R,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,4,9,13,14-pentamethyl-2,3,8,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	MNIOCWIESUAIEQ-HVVQIFGZSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-20(10-9-16-26(2,3)32)21-15-17-30(8)24-13-11-22-23(12-14-25(31)27(22,4)5)28(24,6)18-19-29(21,30)7/h9,11,13,16,20-21,24-25,31-32H,10,12,14-15,17-19H2,1-8H3/b16-9+/t20-,21-,24-,25+,28+,29-,30+/m1/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2C=CC2=C1CC[C@@H](C2(C)C)O)C)C)C/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468165
PubChem CID:	25016915
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids [CHEMONTID:0003233] 3-beta-hydroxysteroids

*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[524802]

☑ 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 NPC238485 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	149
0.1-0.2	1109
0.2-0.3	5069
0.3-0.4	15358
0.4-0.5	9768
0.5-0.6	6829
0.6-0.7	3322
0.7-0.8	912
0.8-0.85	122
0.85-0.9	44
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC231310
0.962	High Similarity	NPC470384
0.9494	High Similarity	NPC202389
0.9494	High Similarity	NPC87489
0.9367	High Similarity	NPC264245
0.925	High Similarity	NPC49964
0.9241	High Similarity	NPC209944
0.9241	High Similarity	NPC164840
0.9241	High Similarity	NPC234193
0.9241	High Similarity	NPC241290
0.9125	High Similarity	NPC47761
0.9114	High Similarity	NPC143182
0.9114	High Similarity	NPC84694
0.9114	High Similarity	NPC30986
0.9114	High Similarity	NPC28862
0.9114	High Similarity	NPC47982
0.9114	High Similarity	NPC81306
0.9114	High Similarity	NPC109546
0.9114	High Similarity	NPC209430
0.907	High Similarity	NPC310013
0.9036	High Similarity	NPC261266
0.9024	High Similarity	NPC205845
0.9012	High Similarity	NPC50964
0.9012	High Similarity	NPC201852
0.9012	High Similarity	NPC218616
0.9012	High Similarity	NPC296701
0.8987	High Similarity	NPC18603
0.8987	High Similarity	NPC76931
0.8987	High Similarity	NPC275910
0.8987	High Similarity	NPC186191
0.8987	High Similarity	NPC307965
0.8987	High Similarity	NPC474216
0.8987	High Similarity	NPC205455
0.8974	High Similarity	NPC470362
0.8916	High Similarity	NPC274448
0.8902	High Similarity	NPC317458
0.8902	High Similarity	NPC475789
0.8902	High Similarity	NPC474634
0.8889	High Similarity	NPC23852
0.8889	High Similarity	NPC6707
0.8889	High Similarity	NPC209620
0.8861	High Similarity	NPC318495
0.8861	High Similarity	NPC155986
0.8861	High Similarity	NPC198968
0.8861	High Similarity	NPC214570
0.8846	High Similarity	NPC471468
0.8824	High Similarity	NPC280556
0.881	High Similarity	NPC6391
0.8795	High Similarity	NPC474047
0.8795	High Similarity	NPC470077
0.878	High Similarity	NPC101462
0.878	High Similarity	NPC189972
0.875	High Similarity	NPC318136
0.875	High Similarity	NPC473943
0.8734	High Similarity	NPC247325
0.8734	High Similarity	NPC244488
0.8734	High Similarity	NPC265588
0.8734	High Similarity	NPC134330
0.8734	High Similarity	NPC321016
0.8734	High Similarity	NPC113733
0.8734	High Similarity	NPC46160
0.8734	High Similarity	NPC73875
0.8734	High Similarity	NPC321381
0.8734	High Similarity	NPC107059
0.8734	High Similarity	NPC129165
0.8734	High Similarity	NPC202642
0.8706	High Similarity	NPC149224
0.869	High Similarity	NPC318390
0.869	High Similarity	NPC157257
0.869	High Similarity	NPC470360
0.8675	High Similarity	NPC82623
0.8659	High Similarity	NPC474683
0.8659	High Similarity	NPC474731
0.8659	High Similarity	NPC7505
0.8659	High Similarity	NPC82986
0.8659	High Similarity	NPC474759
0.8659	High Similarity	NPC474752
0.8642	High Similarity	NPC328714
0.8625	High Similarity	NPC91594
0.8621	High Similarity	NPC295668
0.8621	High Similarity	NPC291484
0.8621	High Similarity	NPC245410
0.8621	High Similarity	NPC192437
0.8621	High Similarity	NPC270511
0.8621	High Similarity	NPC470390
0.8621	High Similarity	NPC80561
0.8621	High Similarity	NPC11216
0.8621	High Similarity	NPC329596
0.8621	High Similarity	NPC3345
0.8621	High Similarity	NPC204188
0.8608	High Similarity	NPC230301
0.8608	High Similarity	NPC304309
0.8608	High Similarity	NPC141071
0.8608	High Similarity	NPC322353
0.8608	High Similarity	NPC285893
0.8608	High Similarity	NPC69383
0.8608	High Similarity	NPC313179
0.8608	High Similarity	NPC121744
0.8608	High Similarity	NPC288035
0.8608	High Similarity	NPC22105
0.8608	High Similarity	NPC134847
0.8608	High Similarity	NPC136188
0.8608	High Similarity	NPC118508
0.8608	High Similarity	NPC257347
0.8608	High Similarity	NPC171148
0.8608	High Similarity	NPC28657
0.8608	High Similarity	NPC471723
0.8608	High Similarity	NPC162742
0.8605	High Similarity	NPC133588
0.8605	High Similarity	NPC474668
0.859	High Similarity	NPC130665
0.8588	High Similarity	NPC152808
0.8588	High Similarity	NPC293287
0.8588	High Similarity	NPC299068
0.8571	High Similarity	NPC474493
0.8571	High Similarity	NPC185568
0.8554	High Similarity	NPC20853
0.8554	High Similarity	NPC470049
0.8523	High Similarity	NPC41554
0.8523	High Similarity	NPC97404
0.8523	High Similarity	NPC471453
0.8523	High Similarity	NPC212948
0.8519	High Similarity	NPC477522
0.8519	High Similarity	NPC167891
0.8519	High Similarity	NPC83351
0.8519	High Similarity	NPC285761
0.8519	High Similarity	NPC87604
0.8506	High Similarity	NPC470361
0.85	High Similarity	NPC189883
0.85	High Similarity	NPC240604
0.85	High Similarity	NPC300324
0.8488	Intermediate Similarity	NPC271967
0.8481	Intermediate Similarity	NPC469533
0.8481	Intermediate Similarity	NPC329090
0.8481	Intermediate Similarity	NPC469593
0.8481	Intermediate Similarity	NPC469534
0.8481	Intermediate Similarity	NPC27395
0.8471	Intermediate Similarity	NPC266511
0.8452	Intermediate Similarity	NPC134481
0.8452	Intermediate Similarity	NPC470558
0.8434	Intermediate Similarity	NPC476646
0.8434	Intermediate Similarity	NPC474531
0.8427	Intermediate Similarity	NPC214697
0.8415	Intermediate Similarity	NPC273410
0.8415	Intermediate Similarity	NPC1319
0.8415	Intermediate Similarity	NPC80530
0.8409	Intermediate Similarity	NPC69622
0.8409	Intermediate Similarity	NPC14380
0.8395	Intermediate Similarity	NPC34019
0.8395	Intermediate Similarity	NPC470711
0.8395	Intermediate Similarity	NPC470758
0.8391	Intermediate Similarity	NPC470542
0.8391	Intermediate Similarity	NPC2158
0.8375	Intermediate Similarity	NPC328104
0.8375	Intermediate Similarity	NPC319090
0.8354	Intermediate Similarity	NPC201373
0.8354	Intermediate Similarity	NPC474140
0.8354	Intermediate Similarity	NPC471799
0.8333	Intermediate Similarity	NPC30166
0.8333	Intermediate Similarity	NPC469406
0.8333	Intermediate Similarity	NPC34834
0.8315	Intermediate Similarity	NPC475806
0.8313	Intermediate Similarity	NPC22403
0.8313	Intermediate Similarity	NPC236237
0.8313	Intermediate Similarity	NPC102253
0.8313	Intermediate Similarity	NPC13554
0.8313	Intermediate Similarity	NPC236112
0.8313	Intermediate Similarity	NPC96362
0.8313	Intermediate Similarity	NPC324772
0.8313	Intermediate Similarity	NPC26117
0.8313	Intermediate Similarity	NPC322313
0.8295	Intermediate Similarity	NPC477606
0.8293	Intermediate Similarity	NPC167037
0.8293	Intermediate Similarity	NPC476314
0.8293	Intermediate Similarity	NPC244385
0.8293	Intermediate Similarity	NPC477514
0.8293	Intermediate Similarity	NPC6978
0.8293	Intermediate Similarity	NPC138621
0.8293	Intermediate Similarity	NPC11908
0.8276	Intermediate Similarity	NPC475772
0.8272	Intermediate Similarity	NPC237460
0.8272	Intermediate Similarity	NPC106432
0.8272	Intermediate Similarity	NPC96319
0.8272	Intermediate Similarity	NPC470749
0.8272	Intermediate Similarity	NPC315261
0.8272	Intermediate Similarity	NPC253190
0.8261	Intermediate Similarity	NPC99726
0.8261	Intermediate Similarity	NPC141401
0.8261	Intermediate Similarity	NPC261807
0.8256	Intermediate Similarity	NPC474083
0.825	Intermediate Similarity	NPC243342
0.825	Intermediate Similarity	NPC477138
0.825	Intermediate Similarity	NPC471797
0.825	Intermediate Similarity	NPC201048
0.825	Intermediate Similarity	NPC476366
0.8242	Intermediate Similarity	NPC259286
0.8235	Intermediate Similarity	NPC82538
0.8235	Intermediate Similarity	NPC237795
0.8228	Intermediate Similarity	NPC242001
0.8228	Intermediate Similarity	NPC110799

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 NPC238485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1251
0.2-0.3	4045
0.3-0.4	2561
0.4-0.5	695
0.5-0.6	218
0.6-0.7	170
0.7-0.8	41
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD7339	Approved
0.8608	High Similarity	NPD8264	Approved
0.8608	High Similarity	NPD6942	Approved
0.8481	Intermediate Similarity	NPD6924	Approved
0.8481	Intermediate Similarity	NPD6926	Approved
0.8313	Intermediate Similarity	NPD7514	Phase 3
0.8313	Intermediate Similarity	NPD6931	Approved
0.8313	Intermediate Similarity	NPD7525	Registered
0.8313	Intermediate Similarity	NPD6930	Phase 2
0.8293	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6933	Approved
0.8228	Intermediate Similarity	NPD7152	Approved
0.8228	Intermediate Similarity	NPD7151	Approved
0.8228	Intermediate Similarity	NPD7150	Approved
0.8193	Intermediate Similarity	NPD6929	Approved
0.8101	Intermediate Similarity	NPD7143	Approved
0.8101	Intermediate Similarity	NPD7144	Approved
0.8095	Intermediate Similarity	NPD4748	Discontinued
0.8095	Intermediate Similarity	NPD7332	Phase 2
0.8072	Intermediate Similarity	NPD7145	Approved
0.8025	Intermediate Similarity	NPD4785	Approved
0.8025	Intermediate Similarity	NPD4784	Approved
0.8023	Intermediate Similarity	NPD6695	Phase 3
0.8	Intermediate Similarity	NPD6902	Approved
0.7975	Intermediate Similarity	NPD6922	Approved
0.7975	Intermediate Similarity	NPD6923	Approved
0.7952	Intermediate Similarity	NPD6925	Approved
0.7952	Intermediate Similarity	NPD6932	Approved
0.7952	Intermediate Similarity	NPD5776	Phase 2
0.7931	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4786	Approved
0.7882	Intermediate Similarity	NPD7509	Discontinued
0.7841	Intermediate Similarity	NPD6893	Approved
0.7778	Intermediate Similarity	NPD4243	Approved
0.7701	Intermediate Similarity	NPD3667	Approved
0.7667	Intermediate Similarity	NPD7524	Approved
0.7667	Intermediate Similarity	NPD7750	Discontinued
0.7586	Intermediate Similarity	NPD6898	Phase 1
0.7558	Intermediate Similarity	NPD6683	Phase 2
0.7558	Intermediate Similarity	NPD7645	Phase 2
0.7556	Intermediate Similarity	NPD5279	Phase 3
0.7527	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7363	Intermediate Similarity	NPD3618	Phase 1
0.7356	Intermediate Similarity	NPD4195	Approved
0.734	Intermediate Similarity	NPD7087	Discontinued
0.7294	Intermediate Similarity	NPD4190	Phase 3
0.7294	Intermediate Similarity	NPD5275	Approved
0.7263	Intermediate Similarity	NPD4202	Approved
0.72	Intermediate Similarity	NPD5211	Phase 2
0.7174	Intermediate Similarity	NPD4694	Approved
0.7174	Intermediate Similarity	NPD5280	Approved
0.7158	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7083	Intermediate Similarity	NPD6399	Phase 3
0.7059	Intermediate Similarity	NPD5141	Approved
0.7041	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5222	Approved
0.7041	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.6989	Remote Similarity	NPD5690	Phase 2
0.6979	Remote Similarity	NPD5284	Approved
0.6979	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5173	Approved
0.697	Remote Similarity	NPD4755	Approved
0.6957	Remote Similarity	NPD3668	Phase 3
0.6947	Remote Similarity	NPD4753	Phase 2
0.6947	Remote Similarity	NPD6051	Approved
0.6931	Remote Similarity	NPD5223	Approved
0.6923	Remote Similarity	NPD4223	Phase 3
0.6923	Remote Similarity	NPD4221	Approved
0.69	Remote Similarity	NPD7638	Approved
0.6882	Remote Similarity	NPD1696	Phase 3
0.6882	Remote Similarity	NPD5329	Approved
0.6882	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7136	Phase 2
0.6875	Remote Similarity	NPD368	Approved
0.6869	Remote Similarity	NPD4697	Phase 3
0.6863	Remote Similarity	NPD5224	Approved
0.6863	Remote Similarity	NPD5225	Approved
0.6863	Remote Similarity	NPD4633	Approved
0.6863	Remote Similarity	NPD5226	Approved
0.6842	Remote Similarity	NPD4518	Approved
0.6832	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD7115	Discovery
0.6809	Remote Similarity	NPD4623	Approved
0.6809	Remote Similarity	NPD4519	Discontinued
0.6804	Remote Similarity	NPD6411	Approved
0.6796	Remote Similarity	NPD5174	Approved
0.6796	Remote Similarity	NPD5175	Approved
0.6774	Remote Similarity	NPD4197	Approved
0.6768	Remote Similarity	NPD4629	Approved
0.6768	Remote Similarity	NPD5210	Approved
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6733	Remote Similarity	NPD5290	Discontinued
0.6706	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4096	Approved
0.6701	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6881	Approved
0.6698	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD4219	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD4732	Discontinued
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4754	Approved
0.6634	Remote Similarity	NPD6083	Phase 2
0.6634	Remote Similarity	NPD6084	Phase 2
0.6633	Remote Similarity	NPD7515	Phase 2
0.6632	Remote Similarity	NPD4689	Approved
0.6632	Remote Similarity	NPD4138	Approved
0.6632	Remote Similarity	NPD4693	Phase 3
0.6632	Remote Similarity	NPD4688	Approved
0.6632	Remote Similarity	NPD4690	Approved
0.6632	Remote Similarity	NPD5205	Approved
0.663	Remote Similarity	NPD4139	Approved
0.663	Remote Similarity	NPD4692	Approved
0.6628	Remote Similarity	NPD4787	Phase 1
0.6604	Remote Similarity	NPD5697	Approved
0.6602	Remote Similarity	NPD4159	Approved
0.66	Remote Similarity	NPD5695	Phase 3
0.6598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6101	Approved
0.6591	Remote Similarity	NPD4687	Approved
0.6591	Remote Similarity	NPD5733	Approved
0.6574	Remote Similarity	NPD7102	Approved
0.6574	Remote Similarity	NPD7290	Approved
0.6574	Remote Similarity	NPD6883	Approved
0.6566	Remote Similarity	NPD5133	Approved
0.6542	Remote Similarity	NPD4729	Approved
0.6542	Remote Similarity	NPD6011	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD4730	Approved
0.6538	Remote Similarity	NPD342	Phase 1
0.6531	Remote Similarity	NPD5207	Approved
0.6522	Remote Similarity	NPD4821	Approved
0.6522	Remote Similarity	NPD4819	Approved
0.6522	Remote Similarity	NPD4822	Approved
0.6522	Remote Similarity	NPD4820	Approved
0.6514	Remote Similarity	NPD6649	Approved
0.6514	Remote Similarity	NPD6847	Approved
0.6514	Remote Similarity	NPD6650	Approved
0.6514	Remote Similarity	NPD8130	Phase 1
0.6514	Remote Similarity	NPD6617	Approved
0.6514	Remote Similarity	NPD6869	Approved
0.6509	Remote Similarity	NPD4767	Approved
0.6509	Remote Similarity	NPD4768	Approved
0.6495	Remote Similarity	NPD4723	Approved
0.6495	Remote Similarity	NPD4722	Approved
0.6489	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD5362	Discontinued
0.6489	Remote Similarity	NPD5331	Approved
0.6481	Remote Similarity	NPD6014	Approved
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD6013	Approved
0.6481	Remote Similarity	NPD6012	Approved
0.6481	Remote Similarity	NPD6372	Approved
0.6465	Remote Similarity	NPD5694	Approved
0.6465	Remote Similarity	NPD6050	Approved
0.6458	Remote Similarity	NPD7521	Approved
0.6458	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5330	Approved
0.6458	Remote Similarity	NPD6684	Approved
0.6458	Remote Similarity	NPD7146	Approved
0.6458	Remote Similarity	NPD7334	Approved
0.6458	Remote Similarity	NPD6409	Approved
0.6455	Remote Similarity	NPD6882	Approved
0.6455	Remote Similarity	NPD8297	Approved
0.6452	Remote Similarity	NPD4790	Discontinued
0.6449	Remote Similarity	NPD5701	Approved
0.6435	Remote Similarity	NPD7503	Approved
0.6422	Remote Similarity	NPD5250	Approved
0.6422	Remote Similarity	NPD5249	Phase 3
0.6422	Remote Similarity	NPD5251	Approved
0.6422	Remote Similarity	NPD4634	Approved
0.6422	Remote Similarity	NPD5247	Approved
0.6422	Remote Similarity	NPD5135	Approved
0.6422	Remote Similarity	NPD5169	Approved
0.6422	Remote Similarity	NPD5248	Approved
0.6422	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4225	Approved
0.6389	Remote Similarity	NPD5168	Approved
0.6389	Remote Similarity	NPD5128	Approved
0.6381	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5127	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