NPASS Compound

Structure

NPC469769 OpenBabel07101718312D 29 32 0 0 1 0 0 0 0 0999 V2000 -6.1235 -4.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.9190 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 1.7321 -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 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 -4.4543 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 0.8660 -0.5000 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 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 18 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 23 2 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 21 4 1 1 0 0 0 21 25 1 0 0 0 0 23 28 1 0 0 0 0 24 14 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 29 1 1 0 0 0 26 29 1 1 0 0 0 27 28 1 1 0 0 0 28 5 1 1 0 0 0 29 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.38
Volume:	470.641
LogP:	8.564
LogD:	7.357
LogS:	-7.372
# Rotatable Bonds:	6
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	4.507
Fsp3:	0.862
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:	-4.859
MDCK Permeability:	6.4640530581527855e-06
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.816
30% Bioavailability (F30%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	95.60089111328125%
Volume Distribution (VD):	2.376
Pgp-substrate:	1.4559149742126465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.229
CYP2D6-substrate:	0.709
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.883

ADMET: Excretion

Clearance (CL):	4.755
Half-life (T1/2):	0.041

ADMET: Toxicity

hERG Blockers:	0.992
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.303
Skin Sensitization:	0.989
Carcinogencity:	0.066
Eye Corrosion:	0.994
Eye Irritation:	0.836
Respiratory Toxicity:	0.62

Download Data

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

Natural Product: NPC469769

Natural Product ID:	NPC469769
*Common Name:**	24-Ethyl Cholesta-3,5-Diene
IUPAC Name:	(8S,9S,10R,13R,14S,17R)-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene
Synonyms:
Standard InCHIKey:	ICCTZARHLGPHMT-WFSFLELISA-N
Standard InCHI:	InChI=1S/C29H48/c1-7-22(20(2)3)12-11-21(4)25-15-16-26-24-14-13-23-10-8-9-18-28(23,5)27(24)17-19-29(25,26)6/h8,10,13,20-22,24-27H,7,9,11-12,14-19H2,1-6H3/t21-,22?,24+,25-,26+,27+,28+,29-/m1/s1
SMILES:	CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC=C4)C)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171156
PubChem CID:	157618
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	whole plant	Cholistan desert near district Bahawalpur (Punjab), Pakistan	2003-Oct	PMID[20542692]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20954	Haloxylon salicornicum	Species	Chenopodiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	100.0	ug.mL-1	PMID[564192]

☑ 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 NPC469769 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	616
0.1-0.2	4071
0.2-0.3	19710
0.3-0.4	10368
0.4-0.5	5637
0.5-0.6	1892
0.6-0.7	358
0.7-0.8	42
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC123194
0.9091	High Similarity	NPC470893
0.8333	Intermediate Similarity	NPC17518
0.8148	Intermediate Similarity	NPC124851
0.8065	Intermediate Similarity	NPC474086
0.8	Intermediate Similarity	NPC22765
0.8	Intermediate Similarity	NPC17810
0.7963	Intermediate Similarity	NPC323445
0.791	Intermediate Similarity	NPC470078
0.7857	Intermediate Similarity	NPC200129
0.7846	Intermediate Similarity	NPC176107
0.7826	Intermediate Similarity	NPC471468
0.7797	Intermediate Similarity	NPC469770
0.7778	Intermediate Similarity	NPC86683
0.7778	Intermediate Similarity	NPC49088
0.7759	Intermediate Similarity	NPC127944
0.7692	Intermediate Similarity	NPC92327
0.7612	Intermediate Similarity	NPC182815
0.7593	Intermediate Similarity	NPC202189
0.7581	Intermediate Similarity	NPC475716
0.7536	Intermediate Similarity	NPC470045
0.7536	Intermediate Similarity	NPC470044
0.75	Intermediate Similarity	NPC475728
0.7463	Intermediate Similarity	NPC20610
0.7424	Intermediate Similarity	NPC176171
0.7407	Intermediate Similarity	NPC192529
0.7391	Intermediate Similarity	NPC115023
0.7344	Intermediate Similarity	NPC469728
0.7286	Intermediate Similarity	NPC251705
0.726	Intermediate Similarity	NPC205455
0.726	Intermediate Similarity	NPC186191
0.726	Intermediate Similarity	NPC18603
0.726	Intermediate Similarity	NPC307965
0.726	Intermediate Similarity	NPC76931
0.7258	Intermediate Similarity	NPC474415
0.7258	Intermediate Similarity	NPC474528
0.7258	Intermediate Similarity	NPC475696
0.7246	Intermediate Similarity	NPC159577
0.7246	Intermediate Similarity	NPC35734
0.7246	Intermediate Similarity	NPC282593
0.7222	Intermediate Similarity	NPC190232
0.7222	Intermediate Similarity	NPC177470
0.7222	Intermediate Similarity	NPC105246
0.7222	Intermediate Similarity	NPC470362
0.7206	Intermediate Similarity	NPC216460
0.7188	Intermediate Similarity	NPC176621
0.7164	Intermediate Similarity	NPC323005
0.7162	Intermediate Similarity	NPC170793
0.7143	Intermediate Similarity	NPC114239
0.7143	Intermediate Similarity	NPC21773
0.7143	Intermediate Similarity	NPC234707
0.7143	Intermediate Similarity	NPC296337
0.7143	Intermediate Similarity	NPC181204
0.7143	Intermediate Similarity	NPC241784
0.7143	Intermediate Similarity	NPC13991
0.7123	Intermediate Similarity	NPC475027
0.7083	Intermediate Similarity	NPC473171
0.7083	Intermediate Similarity	NPC125828
0.7083	Intermediate Similarity	NPC293803
0.7059	Intermediate Similarity	NPC193770
0.7042	Intermediate Similarity	NPC474228
0.7042	Intermediate Similarity	NPC303613
0.7037	Intermediate Similarity	NPC144023
0.7031	Intermediate Similarity	NPC474455
0.7031	Intermediate Similarity	NPC474420
0.7031	Intermediate Similarity	NPC474454
0.7027	Intermediate Similarity	NPC318136
0.7015	Intermediate Similarity	NPC163678
0.7013	Intermediate Similarity	NPC470384
0.7	Intermediate Similarity	NPC477856
0.7	Intermediate Similarity	NPC49422
0.7	Intermediate Similarity	NPC9161
0.7	Intermediate Similarity	NPC40574
0.7	Intermediate Similarity	NPC214770
0.7	Intermediate Similarity	NPC307176
0.6986	Remote Similarity	NPC134330
0.6986	Remote Similarity	NPC202642
0.6986	Remote Similarity	NPC129165
0.6986	Remote Similarity	NPC69408
0.6986	Remote Similarity	NPC46160
0.6986	Remote Similarity	NPC113733
0.6986	Remote Similarity	NPC474463
0.6984	Remote Similarity	NPC474457
0.6974	Remote Similarity	NPC4166
0.6964	Remote Similarity	NPC248411
0.6957	Remote Similarity	NPC160209
0.6957	Remote Similarity	NPC32055
0.6957	Remote Similarity	NPC310992
0.6944	Remote Similarity	NPC309852
0.6944	Remote Similarity	NPC474797
0.6944	Remote Similarity	NPC476904
0.6944	Remote Similarity	NPC474796
0.6944	Remote Similarity	NPC329866
0.6923	Remote Similarity	NPC231310
0.6923	Remote Similarity	NPC238485
0.6912	Remote Similarity	NPC476039
0.6912	Remote Similarity	NPC286669
0.6912	Remote Similarity	NPC222366
0.6909	Remote Similarity	NPC193180
0.6901	Remote Similarity	NPC305501
0.6901	Remote Similarity	NPC265789
0.6901	Remote Similarity	NPC54123
0.6897	Remote Similarity	NPC178644
0.6892	Remote Similarity	NPC475025
0.6892	Remote Similarity	NPC214570
0.6885	Remote Similarity	NPC476679
0.6883	Remote Similarity	NPC311092
0.6883	Remote Similarity	NPC202389
0.6883	Remote Similarity	NPC201852
0.6866	Remote Similarity	NPC469662
0.6857	Remote Similarity	NPC167272
0.6857	Remote Similarity	NPC139397
0.6857	Remote Similarity	NPC269877
0.6852	Remote Similarity	NPC183670
0.6849	Remote Similarity	NPC22105
0.6849	Remote Similarity	NPC257347
0.6849	Remote Similarity	NPC230301
0.6849	Remote Similarity	NPC304309
0.6849	Remote Similarity	NPC288035
0.6849	Remote Similarity	NPC141071
0.6849	Remote Similarity	NPC121744
0.6849	Remote Similarity	NPC471723
0.6849	Remote Similarity	NPC118508
0.6849	Remote Similarity	NPC322353
0.6849	Remote Similarity	NPC134847
0.6849	Remote Similarity	NPC28657
0.6849	Remote Similarity	NPC162742
0.6849	Remote Similarity	NPC136188
0.6849	Remote Similarity	NPC285893
0.6812	Remote Similarity	NPC197805
0.6806	Remote Similarity	NPC474140
0.68	Remote Similarity	NPC275910
0.68	Remote Similarity	NPC470052
0.68	Remote Similarity	NPC82635
0.68	Remote Similarity	NPC105197
0.6795	Remote Similarity	NPC69279
0.6795	Remote Similarity	NPC83569
0.6786	Remote Similarity	NPC227670
0.6786	Remote Similarity	NPC166362
0.6786	Remote Similarity	NPC141777
0.6769	Remote Similarity	NPC309825
0.6761	Remote Similarity	NPC265782
0.6761	Remote Similarity	NPC2634
0.6761	Remote Similarity	NPC251929
0.6761	Remote Similarity	NPC260040
0.6757	Remote Similarity	NPC321016
0.6757	Remote Similarity	NPC107059
0.6757	Remote Similarity	NPC7214
0.6757	Remote Similarity	NPC73875
0.6757	Remote Similarity	NPC474231
0.6757	Remote Similarity	NPC321381
0.6757	Remote Similarity	NPC240604
0.6757	Remote Similarity	NPC189883
0.6757	Remote Similarity	NPC300324
0.6757	Remote Similarity	NPC244488
0.6757	Remote Similarity	NPC247325
0.6753	Remote Similarity	NPC6707
0.6753	Remote Similarity	NPC474122
0.6727	Remote Similarity	NPC103290
0.6721	Remote Similarity	NPC473728
0.6716	Remote Similarity	NPC197238
0.6716	Remote Similarity	NPC202118
0.6714	Remote Similarity	NPC260474
0.6714	Remote Similarity	NPC188292
0.6712	Remote Similarity	NPC255021
0.6711	Remote Similarity	NPC90965
0.6711	Remote Similarity	NPC190211
0.6709	Remote Similarity	NPC87552
0.6667	Remote Similarity	NPC149680
0.6667	Remote Similarity	NPC155986
0.6667	Remote Similarity	NPC279434
0.6667	Remote Similarity	NPC198968
0.6667	Remote Similarity	NPC34019
0.6667	Remote Similarity	NPC87489
0.6667	Remote Similarity	NPC5701
0.6667	Remote Similarity	NPC318495
0.6667	Remote Similarity	NPC91665
0.6667	Remote Similarity	NPC20853
0.6667	Remote Similarity	NPC474230
0.6667	Remote Similarity	NPC223187
0.6625	Remote Similarity	NPC470048
0.6623	Remote Similarity	NPC209944
0.6623	Remote Similarity	NPC234193
0.6623	Remote Similarity	NPC241290
0.6623	Remote Similarity	NPC164840
0.6623	Remote Similarity	NPC474509
0.6622	Remote Similarity	NPC255650
0.662	Remote Similarity	NPC256846
0.662	Remote Similarity	NPC476431
0.6615	Remote Similarity	NPC60772
0.6607	Remote Similarity	NPC473912
0.6579	Remote Similarity	NPC477522
0.6579	Remote Similarity	NPC474216
0.6579	Remote Similarity	NPC87604
0.6579	Remote Similarity	NPC475337
0.6579	Remote Similarity	NPC469996
0.6579	Remote Similarity	NPC473943
0.6579	Remote Similarity	NPC477514
0.6575	Remote Similarity	NPC201373
0.6552	Remote Similarity	NPC229403

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 NPC469769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	546
0.1-0.2	2990
0.2-0.3	4138
0.3-0.4	1049
0.4-0.5	261
0.5-0.6	116
0.6-0.7	42
0.7-0.8	8
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
0.8	Intermediate Similarity	NPD8262	Approved
0.7681	Intermediate Similarity	NPD5733	Approved
0.7681	Intermediate Similarity	NPD4687	Approved
0.7391	Intermediate Similarity	NPD5276	Approved
0.7246	Intermediate Similarity	NPD6938	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6939	Phase 2
0.7222	Intermediate Similarity	NPD1799	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4058	Approved
0.7183	Intermediate Similarity	NPD4785	Approved
0.7183	Intermediate Similarity	NPD4784	Approved
0.7143	Intermediate Similarity	NPD4243	Approved
0.7	Intermediate Similarity	NPD7144	Approved
0.7	Intermediate Similarity	NPD7143	Approved
0.7	Intermediate Similarity	NPD4747	Approved
0.6957	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7150	Approved
0.6901	Remote Similarity	NPD7152	Approved
0.6901	Remote Similarity	NPD7151	Approved
0.6857	Remote Similarity	NPD6922	Approved
0.6857	Remote Similarity	NPD4137	Phase 3
0.6857	Remote Similarity	NPD6923	Approved
0.6849	Remote Similarity	NPD7339	Approved
0.6849	Remote Similarity	NPD6942	Approved
0.6761	Remote Similarity	NPD4691	Approved
0.6622	Remote Similarity	NPD5275	Approved
0.6622	Remote Similarity	NPD4190	Phase 3
0.6582	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4195	Approved
0.6486	Remote Similarity	NPD6924	Approved
0.6486	Remote Similarity	NPD6926	Approved
0.6447	Remote Similarity	NPD6932	Approved
0.6364	Remote Similarity	NPD7145	Approved
0.6341	Remote Similarity	NPD4694	Approved
0.6341	Remote Similarity	NPD5280	Approved
0.6316	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6933	Approved
0.6308	Remote Similarity	NPD4219	Approved
0.6296	Remote Similarity	NPD319	Phase 1
0.6235	Remote Similarity	NPD5207	Approved
0.6234	Remote Similarity	NPD6925	Approved
0.6234	Remote Similarity	NPD5776	Phase 2
0.6203	Remote Similarity	NPD7514	Phase 3
0.6203	Remote Similarity	NPD7525	Registered
0.6184	Remote Similarity	NPD8264	Approved
0.6163	Remote Similarity	NPD5281	Approved
0.6163	Remote Similarity	NPD5694	Approved
0.6163	Remote Similarity	NPD5284	Approved
0.6163	Remote Similarity	NPD6050	Approved
0.6154	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5690	Phase 2
0.6145	Remote Similarity	NPD5279	Phase 3
0.6125	Remote Similarity	NPD6902	Approved
0.6098	Remote Similarity	NPD4786	Approved
0.6076	Remote Similarity	NPD6929	Approved
0.6076	Remote Similarity	NPD6683	Phase 2
0.6049	Remote Similarity	NPD4221	Approved
0.6049	Remote Similarity	NPD4223	Phase 3
0.6047	Remote Similarity	NPD5692	Phase 3
0.6024	Remote Similarity	NPD5329	Approved
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD6931	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.5952	Remote Similarity	NPD6098	Approved
0.5915	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4197	Approved
0.5862	Remote Similarity	NPD4096	Approved
0.5857	Remote Similarity	NPD4194	Approved
0.5857	Remote Similarity	NPD4192	Approved
0.5857	Remote Similarity	NPD4191	Approved
0.5857	Remote Similarity	NPD4193	Approved
0.5854	Remote Similarity	NPD3667	Approved
0.5814	Remote Similarity	NPD5737	Approved
0.5814	Remote Similarity	NPD6672	Approved
0.5814	Remote Similarity	NPD4518	Approved
0.5802	Remote Similarity	NPD7509	Discontinued
0.5802	Remote Similarity	NPD4748	Discontinued
0.5795	Remote Similarity	NPD6079	Approved
0.5783	Remote Similarity	NPD6695	Phase 3
0.5765	Remote Similarity	NPD5205	Approved
0.5765	Remote Similarity	NPD4688	Approved
0.5765	Remote Similarity	NPD5330	Approved
0.5765	Remote Similarity	NPD7521	Approved
0.5765	Remote Similarity	NPD4690	Approved
0.5765	Remote Similarity	NPD7334	Approved
0.5765	Remote Similarity	NPD6684	Approved
0.5765	Remote Similarity	NPD4693	Phase 3
0.5765	Remote Similarity	NPD6409	Approved
0.5765	Remote Similarity	NPD4138	Approved
0.5765	Remote Similarity	NPD7146	Approved
0.5765	Remote Similarity	NPD4689	Approved
0.5747	Remote Similarity	NPD6904	Approved
0.5747	Remote Similarity	NPD6080	Approved
0.5747	Remote Similarity	NPD6673	Approved
0.5747	Remote Similarity	NPD5328	Approved
0.5747	Remote Similarity	NPD6051	Approved
0.5732	Remote Similarity	NPD4692	Approved
0.5732	Remote Similarity	NPD6898	Phase 1
0.5732	Remote Similarity	NPD4139	Approved
0.573	Remote Similarity	NPD5133	Approved
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD3666	Approved
0.5699	Remote Similarity	NPD6404	Discontinued
0.5698	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD7645	Phase 2
0.5652	Remote Similarity	NPD287	Approved
0.5647	Remote Similarity	NPD6893	Approved
0.5632	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD4722	Approved
0.5632	Remote Similarity	NPD4723	Approved
0.5632	Remote Similarity	NPD6903	Approved
0.5632	Remote Similarity	NPD5208	Approved
0.5604	Remote Similarity	NPD5654	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