NPASS Compound

Structure

CID151464 OpenBabel06191715522D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.7893 3.6883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5187 2.4568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8389 -1.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6784 -0.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1959 1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1957 0.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6775 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 1.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8386 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6792 1.9372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 -1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3582 2.9049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6778 -0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3579 1.9367 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5182 0.4839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8395 0.4843 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 -2.5184 1.4524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3211 3.0058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -1.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 5 1 0 0 0 0 4 14 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 13 22 2 0 0 0 0 14 20 1 1 0 0 0 15 23 2 0 0 0 0 16 5 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 6 0 0 0 18 21 1 6 0 0 0 19 20 1 6 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.24
Volume:	349.854
LogP:	4.103
LogD:	4.181
LogS:	-2.6
# Rotatable Bonds:	1
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	4.036
Fsp3:	0.905
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:	-4.776
MDCK Permeability:	1.4471654139924794e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.41
Plasma Protein Binding (PPB):	91.51557159423828%
Volume Distribution (VD):	1.246
Pgp-substrate:	3.1653847694396973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.28
CYP1A2-substrate:	0.418
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.276
CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.761
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.408

ADMET: Excretion

Clearance (CL):	23.184
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.405
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.788
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.402
Maximum Recommended Daily Dose:	0.561
Skin Sensitization:	0.911
Carcinogencity:	0.452
Eye Corrosion:	0.923
Eye Irritation:	0.441
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC151464

Natural Product ID:	NPC151464
*Common Name:**	5Beta-Pregnane-3,20-Dione
IUPAC Name:	(5R,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	XMRPGKVKISIQBV-XWOJZHJZSA-N
Standard InCHI:	InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16+,17-,18+,19+,20+,21-/m1/s1
SMILES:	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486954
PubChem CID:	92745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins 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

☑ 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
Others	6

Activity Type	# Activity
Individual Protein	3
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	log(RBA)	=	1.08	n.a.	PMID[479706]
NPT1462	Individual Protein	Progesterone receptor	Oryctolagus cuniculus	log(RBA)	=	1.08	n.a.	PMID[479706]
NPT896	Individual Protein	Constitutive androstane receptor	Mus musculus	Remaining activity	=	20.0	%	PMID[479703]
NPT24383	SINGLE PROTEIN	Progesterone receptor	Ovis aries	log(RBA)	=	0.6	n.a.	PMID[479706]
NPT2	Others	Unspecified		log(RBA)	=	0.7	n.a.	PMID[479706]
NPT2	Others	Unspecified		Ratio	=	1.2	n.a.	PMID[479707]

☑ 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 NPC151464 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	355
0.1-0.2	8885
0.2-0.3	16999
0.3-0.4	7285
0.4-0.5	5676
0.5-0.6	2688
0.6-0.7	620
0.7-0.8	164
0.8-0.85	18
0.85-0.9	1
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC143597
0.9808	High Similarity	NPC184819
0.9615	High Similarity	NPC288296
0.9615	High Similarity	NPC53245
0.9259	High Similarity	NPC474105
0.8393	Intermediate Similarity	NPC307063
0.8333	Intermediate Similarity	NPC274182
0.8276	Intermediate Similarity	NPC127798
0.8254	Intermediate Similarity	NPC473225
0.8226	Intermediate Similarity	NPC107704
0.8226	Intermediate Similarity	NPC39462
0.8226	Intermediate Similarity	NPC168824
0.8226	Intermediate Similarity	NPC43300
0.8226	Intermediate Similarity	NPC189917
0.8226	Intermediate Similarity	NPC96812
0.8125	Intermediate Similarity	NPC477857
0.8125	Intermediate Similarity	NPC474962
0.8	Intermediate Similarity	NPC108131
0.8	Intermediate Similarity	NPC40574
0.7963	Intermediate Similarity	NPC293343
0.7963	Intermediate Similarity	NPC247786
0.7963	Intermediate Similarity	NPC258672
0.7937	Intermediate Similarity	NPC42060
0.7879	Intermediate Similarity	NPC58057
0.7879	Intermediate Similarity	NPC197701
0.7879	Intermediate Similarity	NPC320549
0.7879	Intermediate Similarity	NPC151018
0.7879	Intermediate Similarity	NPC156277
0.7778	Intermediate Similarity	NPC294440
0.7761	Intermediate Similarity	NPC232112
0.7761	Intermediate Similarity	NPC310766
0.7761	Intermediate Similarity	NPC474123
0.7727	Intermediate Similarity	NPC214770
0.7727	Intermediate Similarity	NPC477856
0.7692	Intermediate Similarity	NPC20610
0.7656	Intermediate Similarity	NPC268736
0.7656	Intermediate Similarity	NPC477931
0.7647	Intermediate Similarity	NPC254340
0.7647	Intermediate Similarity	NPC159497
0.7647	Intermediate Similarity	NPC472854
0.7612	Intermediate Similarity	NPC305501
0.7612	Intermediate Similarity	NPC110615
0.7612	Intermediate Similarity	NPC473267
0.7593	Intermediate Similarity	NPC83187
0.7593	Intermediate Similarity	NPC98246
0.7593	Intermediate Similarity	NPC131981
0.7593	Intermediate Similarity	NPC285814
0.7593	Intermediate Similarity	NPC40249
0.7593	Intermediate Similarity	NPC173996
0.7576	Intermediate Similarity	NPC321732
0.7576	Intermediate Similarity	NPC213178
0.7576	Intermediate Similarity	NPC131892
0.7576	Intermediate Similarity	NPC252032
0.7576	Intermediate Similarity	NPC182815
0.7576	Intermediate Similarity	NPC469941
0.7576	Intermediate Similarity	NPC324607
0.7576	Intermediate Similarity	NPC319671
0.7576	Intermediate Similarity	NPC476734
0.7576	Intermediate Similarity	NPC196197
0.7576	Intermediate Similarity	NPC6120
0.7576	Intermediate Similarity	NPC327728
0.7538	Intermediate Similarity	NPC474221
0.7538	Intermediate Similarity	NPC130459
0.7538	Intermediate Similarity	NPC478180
0.7536	Intermediate Similarity	NPC125767
0.7536	Intermediate Similarity	NPC174964
0.7536	Intermediate Similarity	NPC255650
0.7536	Intermediate Similarity	NPC21220
0.7536	Intermediate Similarity	NPC195155
0.7536	Intermediate Similarity	NPC97534
0.7536	Intermediate Similarity	NPC273366
0.7536	Intermediate Similarity	NPC72444
0.75	Intermediate Similarity	NPC474228
0.75	Intermediate Similarity	NPC303613
0.7463	Intermediate Similarity	NPC307176
0.7463	Intermediate Similarity	NPC159577
0.7463	Intermediate Similarity	NPC476731
0.7463	Intermediate Similarity	NPC282593
0.7463	Intermediate Similarity	NPC35734
0.7463	Intermediate Similarity	NPC477929
0.7455	Intermediate Similarity	NPC20017
0.7429	Intermediate Similarity	NPC472486
0.7429	Intermediate Similarity	NPC5767
0.7429	Intermediate Similarity	NPC475742
0.7429	Intermediate Similarity	NPC472487
0.7391	Intermediate Similarity	NPC255021
0.7391	Intermediate Similarity	NPC167702
0.7391	Intermediate Similarity	NPC280026
0.7385	Intermediate Similarity	NPC323005
0.7353	Intermediate Similarity	NPC470078
0.7353	Intermediate Similarity	NPC115023
0.7353	Intermediate Similarity	NPC234707
0.7353	Intermediate Similarity	NPC89310
0.7353	Intermediate Similarity	NPC223187
0.7353	Intermediate Similarity	NPC469940
0.7353	Intermediate Similarity	NPC472309
0.7353	Intermediate Similarity	NPC126642
0.7324	Intermediate Similarity	NPC91665
0.7324	Intermediate Similarity	NPC23884
0.7324	Intermediate Similarity	NPC264602
0.7324	Intermediate Similarity	NPC221420
0.7324	Intermediate Similarity	NPC470557
0.7324	Intermediate Similarity	NPC477918
0.7324	Intermediate Similarity	NPC475031
0.7313	Intermediate Similarity	NPC139397
0.7313	Intermediate Similarity	NPC64466
0.7286	Intermediate Similarity	NPC293803
0.7286	Intermediate Similarity	NPC27349
0.7286	Intermediate Similarity	NPC472311
0.7286	Intermediate Similarity	NPC212733
0.7286	Intermediate Similarity	NPC24014
0.7246	Intermediate Similarity	NPC251705
0.7246	Intermediate Similarity	NPC52667
0.7222	Intermediate Similarity	NPC63020
0.7222	Intermediate Similarity	NPC478128
0.7222	Intermediate Similarity	NPC185465
0.7206	Intermediate Similarity	NPC265782
0.7206	Intermediate Similarity	NPC477850
0.7206	Intermediate Similarity	NPC260040
0.7206	Intermediate Similarity	NPC2634
0.7206	Intermediate Similarity	NPC251929
0.7183	Intermediate Similarity	NPC69408
0.7183	Intermediate Similarity	NPC471046
0.7183	Intermediate Similarity	NPC4209
0.7164	Intermediate Similarity	NPC180777
0.7164	Intermediate Similarity	NPC2568
0.7164	Intermediate Similarity	NPC469724
0.7164	Intermediate Similarity	NPC260319
0.7164	Intermediate Similarity	NPC475977
0.7164	Intermediate Similarity	NPC474954
0.7164	Intermediate Similarity	NPC103647
0.7164	Intermediate Similarity	NPC100917
0.7164	Intermediate Similarity	NPC31187
0.7164	Intermediate Similarity	NPC281203
0.7143	Intermediate Similarity	NPC309852
0.7143	Intermediate Similarity	NPC270042
0.7143	Intermediate Similarity	NPC133922
0.7143	Intermediate Similarity	NPC477930
0.7123	Intermediate Similarity	NPC320144
0.7123	Intermediate Similarity	NPC201459
0.7123	Intermediate Similarity	NPC52951
0.7123	Intermediate Similarity	NPC192744
0.7123	Intermediate Similarity	NPC245029
0.7123	Intermediate Similarity	NPC31302
0.7123	Intermediate Similarity	NPC215843
0.7115	Intermediate Similarity	NPC45270
0.7115	Intermediate Similarity	NPC135077
0.7115	Intermediate Similarity	NPC215118
0.7115	Intermediate Similarity	NPC59570
0.7101	Intermediate Similarity	NPC54123
0.7083	Intermediate Similarity	NPC207010
0.7083	Intermediate Similarity	NPC298168
0.7083	Intermediate Similarity	NPC66105
0.7083	Intermediate Similarity	NPC477919
0.7083	Intermediate Similarity	NPC143133
0.7083	Intermediate Similarity	NPC317913
0.7083	Intermediate Similarity	NPC180199
0.7077	Intermediate Similarity	NPC128608
0.7059	Intermediate Similarity	NPC286814
0.7042	Intermediate Similarity	NPC159789
0.7042	Intermediate Similarity	NPC477934
0.7037	Intermediate Similarity	NPC171783
0.7027	Intermediate Similarity	NPC470609
0.7027	Intermediate Similarity	NPC472853
0.7027	Intermediate Similarity	NPC474509
0.7015	Intermediate Similarity	NPC220210
0.7015	Intermediate Similarity	NPC20181
0.7	Intermediate Similarity	NPC279241
0.7	Intermediate Similarity	NPC470045
0.7	Intermediate Similarity	NPC470044
0.6986	Remote Similarity	NPC82635
0.6986	Remote Similarity	NPC329117
0.6986	Remote Similarity	NPC34046
0.6986	Remote Similarity	NPC199965
0.6986	Remote Similarity	NPC324700
0.6986	Remote Similarity	NPC470052
0.6986	Remote Similarity	NPC476732
0.6986	Remote Similarity	NPC224802
0.6986	Remote Similarity	NPC80089
0.6986	Remote Similarity	NPC171426
0.6944	Remote Similarity	NPC477932
0.6944	Remote Similarity	NPC246445
0.6944	Remote Similarity	NPC477933
0.6933	Remote Similarity	NPC77311
0.6933	Remote Similarity	NPC474484
0.6933	Remote Similarity	NPC472230
0.6933	Remote Similarity	NPC472229
0.6933	Remote Similarity	NPC469745
0.6933	Remote Similarity	NPC103754
0.6923	Remote Similarity	NPC472306
0.6912	Remote Similarity	NPC142754
0.6912	Remote Similarity	NPC82477
0.6912	Remote Similarity	NPC296697
0.6912	Remote Similarity	NPC39157
0.6912	Remote Similarity	NPC470956
0.6901	Remote Similarity	NPC329866
0.6901	Remote Similarity	NPC474796
0.6901	Remote Similarity	NPC474797
0.6892	Remote Similarity	NPC201276
0.6892	Remote Similarity	NPC80891

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 NPC151464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	5210
0.2-0.3	2640
0.3-0.4	447
0.4-0.5	243
0.5-0.6	132
0.6-0.7	48
0.7-0.8	25
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8254	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD5360	Phase 3
0.8	Intermediate Similarity	NPD4789	Approved
0.7937	Intermediate Similarity	NPD4224	Phase 2
0.7879	Intermediate Similarity	NPD6081	Approved
0.7879	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4245	Approved
0.7727	Intermediate Similarity	NPD4244	Approved
0.7612	Intermediate Similarity	NPD4758	Discontinued
0.7612	Intermediate Similarity	NPD5777	Approved
0.7593	Intermediate Similarity	NPD345	Approved
0.7593	Intermediate Similarity	NPD344	Approved
0.7593	Intermediate Similarity	NPD343	Approved
0.7576	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3698	Phase 2
0.7576	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4747	Approved
0.7391	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4137	Phase 3
0.7222	Intermediate Similarity	NPD5364	Discontinued
0.7206	Intermediate Similarity	NPD4691	Approved
0.7183	Intermediate Similarity	NPD6117	Approved
0.7164	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5733	Approved
0.7083	Intermediate Similarity	NPD6116	Phase 1
0.7042	Intermediate Similarity	NPD3703	Phase 2
0.6986	Remote Similarity	NPD6115	Approved
0.6986	Remote Similarity	NPD6697	Approved
0.6986	Remote Similarity	NPD4776	Phase 2
0.6986	Remote Similarity	NPD6118	Approved
0.6986	Remote Similarity	NPD6114	Approved
0.6986	Remote Similarity	NPD4777	Suspended
0.6901	Remote Similarity	NPD4687	Approved
0.6901	Remote Similarity	NPD4058	Approved
0.6857	Remote Similarity	NPD5276	Approved
0.6806	Remote Similarity	NPD3702	Approved
0.6757	Remote Similarity	NPD3671	Phase 1
0.6753	Remote Similarity	NPD4788	Approved
0.6533	Remote Similarity	NPD3617	Approved
0.6456	Remote Similarity	NPD4786	Approved
0.641	Remote Similarity	NPD4221	Approved
0.641	Remote Similarity	NPD4223	Phase 3
0.6375	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5329	Approved
0.6296	Remote Similarity	NPD6098	Approved
0.6282	Remote Similarity	NPD4139	Approved
0.6282	Remote Similarity	NPD4692	Approved
0.625	Remote Similarity	NPD4197	Approved
0.6234	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3667	Approved
0.6145	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5737	Approved
0.6145	Remote Similarity	NPD6672	Approved
0.6111	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD4688	Approved
0.6098	Remote Similarity	NPD4693	Phase 3
0.6098	Remote Similarity	NPD4690	Approved
0.6098	Remote Similarity	NPD4138	Approved
0.6098	Remote Similarity	NPD4689	Approved
0.6098	Remote Similarity	NPD7334	Approved
0.6098	Remote Similarity	NPD7521	Approved
0.6098	Remote Similarity	NPD6409	Approved
0.6098	Remote Similarity	NPD5330	Approved
0.6098	Remote Similarity	NPD7146	Approved
0.6098	Remote Similarity	NPD5205	Approved
0.6098	Remote Similarity	NPD6684	Approved
0.6076	Remote Similarity	NPD8028	Phase 2
0.6071	Remote Similarity	NPD6080	Approved
0.6071	Remote Similarity	NPD5328	Approved
0.6071	Remote Similarity	NPD6904	Approved
0.6071	Remote Similarity	NPD6673	Approved
0.6049	Remote Similarity	NPD3668	Phase 3
0.6049	Remote Similarity	NPD3665	Phase 1
0.6049	Remote Similarity	NPD3133	Approved
0.6049	Remote Similarity	NPD3666	Approved
0.6027	Remote Similarity	NPD4787	Phase 1
0.5952	Remote Similarity	NPD5208	Approved
0.5952	Remote Similarity	NPD6903	Approved
0.593	Remote Similarity	NPD8034	Phase 2
0.593	Remote Similarity	NPD8035	Phase 2
0.593	Remote Similarity	NPD6079	Approved
0.5926	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3618	Phase 1
0.5904	Remote Similarity	NPD4694	Approved
0.5904	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD5280	Approved
0.5904	Remote Similarity	NPD5690	Phase 2
0.5882	Remote Similarity	NPD4753	Phase 2
0.5862	Remote Similarity	NPD6399	Phase 3
0.5795	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD5693	Phase 1
0.5747	Remote Similarity	NPD6050	Approved
0.5735	Remote Similarity	NPD3198	Approved
0.573	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5279	Phase 3
0.5692	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD4202	Approved
0.5632	Remote Similarity	NPD6934	Discontinued
0.5632	Remote Similarity	NPD5207	Approved
0.5632	Remote Similarity	NPD5692	Phase 3
0.5625	Remote Similarity	NPD4195	Approved
0.5618	Remote Similarity	NPD6001	Approved
0.5604	Remote Similarity	NPD6083	Phase 2
0.5604	Remote Similarity	NPD6084	Phase 2

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