NPASS Compound

Structure

NPC475728 OpenBabel07101718222D 29 32 0 0 1 0 0 0 0 0999 V2000 0.1293 5.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 3.4895 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 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 1.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 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 -0.9000 2.9543 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 3.4641 -1.0000 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 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 4.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 3.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 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 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2111 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 16 2 0 0 0 0 9 21 2 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 21 26 1 0 0 0 0 22 11 1 1 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 27 1 6 0 0 0 24 26 1 6 0 0 0 25 27 1 6 0 0 0 25 28 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 28 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.34
Volume:	459.499
LogP:	7.367
LogD:	5.075
LogS:	-4.912
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.821
Fsp3:	0.786
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:	-4.47
MDCK Permeability:	1.8509108485886827e-05
Pgp-inhibitor:	0.738
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.804
30% Bioavailability (F30%):	0.098

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	95.59528350830078%
Volume Distribution (VD):	1.308
Pgp-substrate:	2.587014675140381%

ADMET: Metabolism

CYP1A2-inhibitor:	0.258
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.213
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.297
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.964
CYP3A4-substrate:	0.702

ADMET: Excretion

Clearance (CL):	13.635
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.292
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.273
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.897
Maximum Recommended Daily Dose:	0.776
Skin Sensitization:	0.906
Carcinogencity:	0.928
Eye Corrosion:	0.048
Eye Irritation:	0.225
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: NPC475728

Natural Product ID:	NPC475728
*Common Name:**	(20S)-20-Hydroxyergosta-1,4,24(28)-Trien-3-One
IUPAC Name:	(2S)-2-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptan-2-ol
Synonyms:
Standard InCHIKey:	CKQHQYJORUBIMM-RMIXPHLWSA-N
Standard InCHI:	InChI=1S/C28H44O/c1-19(2)20(3)14-18-28(6,29)25-13-12-23-22-11-10-21-9-7-8-16-26(21,4)24(22)15-17-27(23,25)5/h8-9,16,19,22-25,29H,3,7,10-15,17-18H2,1-2,4-6H3/t22-,23-,24-,25-,26-,27-,28-/m0/s1
SMILES:	CC(C(=C)CC[C@@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CCC=C[C@]12C)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513038
PubChem CID:	44559217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[16038562]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	23400.0	nM	PMID[500903]

☑ 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 NPC475728 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	1537
0.2-0.3	11043
0.3-0.4	14076
0.4-0.5	6679
0.5-0.6	5589
0.6-0.7	2737
0.7-0.8	724
0.8-0.85	113
0.85-0.9	44
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9014	High Similarity	NPC134330
0.9014	High Similarity	NPC129165
0.9014	High Similarity	NPC113733
0.8889	High Similarity	NPC318495
0.8889	High Similarity	NPC155986
0.8889	High Similarity	NPC198968
0.8873	High Similarity	NPC134847
0.8873	High Similarity	NPC304309
0.8873	High Similarity	NPC288035
0.8873	High Similarity	NPC141071
0.8873	High Similarity	NPC471723
0.8873	High Similarity	NPC230301
0.8873	High Similarity	NPC162742
0.8873	High Similarity	NPC22105
0.8873	High Similarity	NPC285893
0.8873	High Similarity	NPC257347
0.8873	High Similarity	NPC136188
0.8873	High Similarity	NPC28657
0.8824	High Similarity	NPC160209
0.8806	High Similarity	NPC279434
0.8784	High Similarity	NPC209944
0.8784	High Similarity	NPC241290
0.8784	High Similarity	NPC164840
0.8767	High Similarity	NPC307965
0.8767	High Similarity	NPC76931
0.8767	High Similarity	NPC18603
0.875	High Similarity	NPC240604
0.875	High Similarity	NPC247325
0.875	High Similarity	NPC189883
0.875	High Similarity	NPC470362
0.875	High Similarity	NPC300324
0.875	High Similarity	NPC107059
0.875	High Similarity	NPC321381
0.875	High Similarity	NPC244488
0.875	High Similarity	NPC321016
0.8676	High Similarity	NPC197805
0.8667	High Similarity	NPC264245
0.8667	High Similarity	NPC47761
0.8649	High Similarity	NPC328714
0.863	High Similarity	NPC34019
0.8615	High Similarity	NPC135648
0.8615	High Similarity	NPC323153
0.8611	High Similarity	NPC471468
0.8592	High Similarity	NPC474140
0.8553	High Similarity	NPC49964
0.8551	High Similarity	NPC94192
0.8533	High Similarity	NPC234193
0.8529	High Similarity	NPC286669
0.8529	High Similarity	NPC476039
0.8529	High Similarity	NPC222366
0.8514	High Similarity	NPC477522
0.8514	High Similarity	NPC87604
0.8514	High Similarity	NPC285761
0.8514	High Similarity	NPC473943
0.8514	High Similarity	NPC477514
0.8514	High Similarity	NPC474216
0.8493	Intermediate Similarity	NPC46160
0.8493	Intermediate Similarity	NPC202642
0.8493	Intermediate Similarity	NPC237460
0.8462	Intermediate Similarity	NPC5698
0.8429	Intermediate Similarity	NPC476431
0.84	Intermediate Similarity	NPC215843
0.84	Intermediate Similarity	NPC84694
0.84	Intermediate Similarity	NPC109546
0.84	Intermediate Similarity	NPC209430
0.84	Intermediate Similarity	NPC30986
0.84	Intermediate Similarity	NPC81306
0.84	Intermediate Similarity	NPC1319
0.84	Intermediate Similarity	NPC47982
0.84	Intermediate Similarity	NPC273410
0.84	Intermediate Similarity	NPC80530
0.84	Intermediate Similarity	NPC28862
0.84	Intermediate Similarity	NPC143182
0.8378	Intermediate Similarity	NPC214570
0.8356	Intermediate Similarity	NPC322353
0.8356	Intermediate Similarity	NPC121744
0.8356	Intermediate Similarity	NPC118508
0.8333	Intermediate Similarity	NPC470077
0.8333	Intermediate Similarity	NPC205845
0.8333	Intermediate Similarity	NPC182717
0.8333	Intermediate Similarity	NPC471799
0.8312	Intermediate Similarity	NPC50964
0.8312	Intermediate Similarity	NPC30166
0.8312	Intermediate Similarity	NPC218616
0.8312	Intermediate Similarity	NPC87489
0.8312	Intermediate Similarity	NPC296701
0.831	Intermediate Similarity	NPC145498
0.8289	Intermediate Similarity	NPC26117
0.8289	Intermediate Similarity	NPC322313
0.8289	Intermediate Similarity	NPC236237
0.8289	Intermediate Similarity	NPC102253
0.8289	Intermediate Similarity	NPC13554
0.8289	Intermediate Similarity	NPC236112
0.8286	Intermediate Similarity	NPC32055
0.8267	Intermediate Similarity	NPC275910
0.8267	Intermediate Similarity	NPC302041
0.8267	Intermediate Similarity	NPC65897
0.8267	Intermediate Similarity	NPC85346
0.8267	Intermediate Similarity	NPC186191
0.8267	Intermediate Similarity	NPC244385
0.8267	Intermediate Similarity	NPC138621
0.8267	Intermediate Similarity	NPC205455
0.8267	Intermediate Similarity	NPC167037
0.8267	Intermediate Similarity	NPC6978
0.8243	Intermediate Similarity	NPC96319
0.8243	Intermediate Similarity	NPC474231
0.8243	Intermediate Similarity	NPC73875
0.8228	Intermediate Similarity	NPC318390
0.8228	Intermediate Similarity	NPC274448
0.8228	Intermediate Similarity	NPC157257
0.8219	Intermediate Similarity	NPC471797
0.8219	Intermediate Similarity	NPC27395
0.8219	Intermediate Similarity	NPC469593
0.8219	Intermediate Similarity	NPC469534
0.8219	Intermediate Similarity	NPC329090
0.8219	Intermediate Similarity	NPC469533
0.8209	Intermediate Similarity	NPC41160
0.8205	Intermediate Similarity	NPC474634
0.8205	Intermediate Similarity	NPC475789
0.8194	Intermediate Similarity	NPC242001
0.8182	Intermediate Similarity	NPC474531
0.8182	Intermediate Similarity	NPC474759
0.8182	Intermediate Similarity	NPC470383
0.8182	Intermediate Similarity	NPC70927
0.8182	Intermediate Similarity	NPC474683
0.8182	Intermediate Similarity	NPC23852
0.8182	Intermediate Similarity	NPC82986
0.8182	Intermediate Similarity	NPC474752
0.8182	Intermediate Similarity	NPC7505
0.8182	Intermediate Similarity	NPC209620
0.8182	Intermediate Similarity	NPC147066
0.8182	Intermediate Similarity	NPC474731
0.8133	Intermediate Similarity	NPC475027
0.8133	Intermediate Similarity	NPC475025
0.8133	Intermediate Similarity	NPC474230
0.8125	Intermediate Similarity	NPC261266
0.8116	Intermediate Similarity	NPC163678
0.8116	Intermediate Similarity	NPC64123
0.8116	Intermediate Similarity	NPC476737
0.8116	Intermediate Similarity	NPC27243
0.8108	Intermediate Similarity	NPC328104
0.8108	Intermediate Similarity	NPC319090
0.8101	Intermediate Similarity	NPC231310
0.8101	Intermediate Similarity	NPC238485
0.8101	Intermediate Similarity	NPC474047
0.8101	Intermediate Similarity	NPC33913
0.8088	Intermediate Similarity	NPC174956
0.8082	Intermediate Similarity	NPC474743
0.8082	Intermediate Similarity	NPC201373
0.8077	Intermediate Similarity	NPC5985
0.8077	Intermediate Similarity	NPC101462
0.8077	Intermediate Similarity	NPC1272
0.8077	Intermediate Similarity	NPC189972
0.8077	Intermediate Similarity	NPC470049
0.8077	Intermediate Similarity	NPC193347
0.8077	Intermediate Similarity	NPC470614
0.806	Intermediate Similarity	NPC252809
0.8056	Intermediate Similarity	NPC49422
0.8056	Intermediate Similarity	NPC9161
0.8028	Intermediate Similarity	NPC216460
0.8028	Intermediate Similarity	NPC208999
0.8026	Intermediate Similarity	NPC318136
0.8026	Intermediate Similarity	NPC312328
0.8025	Intermediate Similarity	NPC149224
0.8	Intermediate Similarity	NPC470360
0.8	Intermediate Similarity	NPC315261
0.8	Intermediate Similarity	NPC39068
0.8	Intermediate Similarity	NPC179024
0.8	Intermediate Similarity	NPC474189
0.8	Intermediate Similarity	NPC264779
0.8	Intermediate Similarity	NPC149680
0.8	Intermediate Similarity	NPC29447
0.8	Intermediate Similarity	NPC474349
0.7975	Intermediate Similarity	NPC207013
0.7975	Intermediate Similarity	NPC82623
0.7975	Intermediate Similarity	NPC470558
0.7975	Intermediate Similarity	NPC470384
0.7975	Intermediate Similarity	NPC134481
0.7975	Intermediate Similarity	NPC317458
0.7975	Intermediate Similarity	NPC477818
0.7975	Intermediate Similarity	NPC477852
0.7973	Intermediate Similarity	NPC243342
0.7973	Intermediate Similarity	NPC477138
0.7973	Intermediate Similarity	NPC91858
0.7973	Intermediate Similarity	NPC100334
0.7949	Intermediate Similarity	NPC201912
0.7949	Intermediate Similarity	NPC6434
0.7949	Intermediate Similarity	NPC6707
0.7949	Intermediate Similarity	NPC38350
0.7945	Intermediate Similarity	NPC111234
0.7945	Intermediate Similarity	NPC167706
0.7945	Intermediate Similarity	NPC110799
0.7941	Intermediate Similarity	NPC194208
0.7941	Intermediate Similarity	NPC79576
0.7941	Intermediate Similarity	NPC282694
0.7927	Intermediate Similarity	NPC133588
0.7922	Intermediate Similarity	NPC477371
0.7917	Intermediate Similarity	NPC167272
0.7917	Intermediate Similarity	NPC269877
0.7901	Intermediate Similarity	NPC293287

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 NPC475728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1695
0.2-0.3	4671
0.3-0.4	1851
0.4-0.5	394
0.5-0.6	140
0.6-0.7	146
0.7-0.8	73
0.8-0.85	14
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9559	High Similarity	NPD4784	Approved
0.9559	High Similarity	NPD4785	Approved
0.9552	High Similarity	NPD4243	Approved
0.8873	High Similarity	NPD7339	Approved
0.8873	High Similarity	NPD4190	Phase 3
0.8873	High Similarity	NPD5275	Approved
0.8873	High Similarity	NPD6942	Approved
0.8649	High Similarity	NPD4195	Approved
0.8289	Intermediate Similarity	NPD7525	Registered
0.8243	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD6924	Approved
0.8219	Intermediate Similarity	NPD6926	Approved
0.8077	Intermediate Similarity	NPD4221	Approved
0.8077	Intermediate Similarity	NPD4223	Phase 3
0.8056	Intermediate Similarity	NPD7144	Approved
0.8056	Intermediate Similarity	NPD7143	Approved
0.8	Intermediate Similarity	NPD6933	Approved
0.8	Intermediate Similarity	NPD5329	Approved
0.7945	Intermediate Similarity	NPD7152	Approved
0.7945	Intermediate Similarity	NPD7150	Approved
0.7945	Intermediate Similarity	NPD7151	Approved
0.7917	Intermediate Similarity	NPD6922	Approved
0.7917	Intermediate Similarity	NPD6923	Approved
0.7875	Intermediate Similarity	NPD4197	Approved
0.7875	Intermediate Similarity	NPD4786	Approved
0.7683	Intermediate Similarity	NPD5205	Approved
0.7683	Intermediate Similarity	NPD4688	Approved
0.7683	Intermediate Similarity	NPD4689	Approved
0.7683	Intermediate Similarity	NPD4690	Approved
0.7683	Intermediate Similarity	NPD4138	Approved
0.7683	Intermediate Similarity	NPD4693	Phase 3
0.7683	Intermediate Similarity	NPD5690	Phase 2
0.7662	Intermediate Similarity	NPD6932	Approved
0.7625	Intermediate Similarity	NPD3667	Approved
0.7595	Intermediate Similarity	NPD6931	Approved
0.7595	Intermediate Similarity	NPD6930	Phase 2
0.759	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4722	Approved
0.75	Intermediate Similarity	NPD4723	Approved
0.747	Intermediate Similarity	NPD5280	Approved
0.747	Intermediate Similarity	NPD4694	Approved
0.7468	Intermediate Similarity	NPD6929	Approved
0.7468	Intermediate Similarity	NPD7645	Phase 2
0.7442	Intermediate Similarity	NPD6079	Approved
0.7439	Intermediate Similarity	NPD3665	Phase 1
0.7439	Intermediate Similarity	NPD3666	Approved
0.7439	Intermediate Similarity	NPD3133	Approved
0.7412	Intermediate Similarity	NPD5328	Approved
0.7412	Intermediate Similarity	NPD4753	Phase 2
0.7375	Intermediate Similarity	NPD7514	Phase 3
0.7375	Intermediate Similarity	NPD7509	Discontinued
0.7375	Intermediate Similarity	NPD4748	Discontinued
0.7342	Intermediate Similarity	NPD3617	Approved
0.7342	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7145	Approved
0.7317	Intermediate Similarity	NPD6695	Phase 3
0.7284	Intermediate Similarity	NPD4139	Approved
0.7284	Intermediate Similarity	NPD4692	Approved
0.7262	Intermediate Similarity	NPD3618	Phase 1
0.7262	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6098	Approved
0.7262	Intermediate Similarity	NPD4623	Approved
0.7262	Intermediate Similarity	NPD4519	Discontinued
0.725	Intermediate Similarity	NPD6683	Phase 2
0.7241	Intermediate Similarity	NPD5281	Approved
0.7241	Intermediate Similarity	NPD5284	Approved
0.7229	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5776	Phase 2
0.7215	Intermediate Similarity	NPD6925	Approved
0.7191	Intermediate Similarity	NPD4629	Approved
0.7191	Intermediate Similarity	NPD5210	Approved
0.716	Intermediate Similarity	NPD7332	Phase 2
0.7159	Intermediate Similarity	NPD6399	Phase 3
0.7159	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD6893	Approved
0.7108	Intermediate Similarity	NPD4788	Approved
0.7105	Intermediate Similarity	NPD4747	Approved
0.7073	Intermediate Similarity	NPD6902	Approved
0.7067	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5279	Phase 3
0.7033	Intermediate Similarity	NPD6084	Phase 2
0.7033	Intermediate Similarity	NPD6083	Phase 2
0.7024	Intermediate Similarity	NPD3668	Phase 3
0.7011	Intermediate Similarity	NPD6904	Approved
0.7011	Intermediate Similarity	NPD6080	Approved
0.7011	Intermediate Similarity	NPD6673	Approved
0.7011	Intermediate Similarity	NPD6051	Approved
0.6977	Remote Similarity	NPD7750	Discontinued
0.6977	Remote Similarity	NPD7524	Approved
0.6974	Remote Similarity	NPD4137	Phase 3
0.6951	Remote Similarity	NPD4695	Discontinued
0.6932	Remote Similarity	NPD4096	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5222	Approved
0.6897	Remote Similarity	NPD5737	Approved
0.6897	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD4518	Approved
0.6897	Remote Similarity	NPD5208	Approved
0.6883	Remote Similarity	NPD6939	Phase 2
0.6883	Remote Similarity	NPD4691	Approved
0.6883	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4696	Approved
0.6882	Remote Similarity	NPD5285	Approved
0.6882	Remote Similarity	NPD5286	Approved
0.6867	Remote Similarity	NPD6898	Phase 1
0.686	Remote Similarity	NPD5330	Approved
0.686	Remote Similarity	NPD7334	Approved
0.686	Remote Similarity	NPD7146	Approved
0.686	Remote Similarity	NPD6409	Approved
0.686	Remote Similarity	NPD7521	Approved
0.686	Remote Similarity	NPD6684	Approved
0.6848	Remote Similarity	NPD5173	Approved
0.6848	Remote Similarity	NPD4755	Approved
0.6835	Remote Similarity	NPD4058	Approved
0.6835	Remote Similarity	NPD4687	Approved
0.6835	Remote Similarity	NPD5733	Approved
0.6813	Remote Similarity	NPD5695	Phase 3
0.6809	Remote Similarity	NPD5223	Approved
0.6778	Remote Similarity	NPD5133	Approved
0.6774	Remote Similarity	NPD5696	Approved
0.675	Remote Similarity	NPD8264	Approved
0.6744	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5207	Approved
0.6742	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4697	Phase 3
0.6737	Remote Similarity	NPD5211	Phase 2
0.6737	Remote Similarity	NPD5226	Approved
0.6737	Remote Similarity	NPD5224	Approved
0.6737	Remote Similarity	NPD4633	Approved
0.6737	Remote Similarity	NPD5225	Approved
0.6737	Remote Similarity	NPD5091	Approved
0.6705	Remote Similarity	NPD6903	Approved
0.6705	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5707	Approved
0.6702	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.663	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5360	Phase 3
0.6623	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5141	Approved
0.6596	Remote Similarity	NPD5290	Discontinued
0.6582	Remote Similarity	NPD5276	Approved
0.6566	Remote Similarity	NPD6881	Approved
0.6566	Remote Similarity	NPD6899	Approved
0.6556	Remote Similarity	NPD5692	Phase 3
0.6538	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6402	Approved
0.6531	Remote Similarity	NPD6675	Approved
0.6531	Remote Similarity	NPD7128	Approved
0.6531	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD5771	Approved
0.6522	Remote Similarity	NPD6001	Approved
0.6495	Remote Similarity	NPD4754	Approved
0.6484	Remote Similarity	NPD7515	Phase 2
0.6465	Remote Similarity	NPD5697	Approved
0.6463	Remote Similarity	NPD1346	Approved
0.6456	Remote Similarity	NPD4787	Phase 1
0.6444	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7102	Approved
0.6436	Remote Similarity	NPD6883	Approved
0.6436	Remote Similarity	NPD7290	Approved
0.6421	Remote Similarity	NPD7638	Approved
0.6404	Remote Similarity	NPD3573	Approved
0.64	Remote Similarity	NPD4729	Approved
0.64	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD4730	Approved
0.64	Remote Similarity	NPD7320	Approved
0.6373	Remote Similarity	NPD6650	Approved
0.6373	Remote Similarity	NPD6649	Approved
0.6373	Remote Similarity	NPD6847	Approved
0.6373	Remote Similarity	NPD6869	Approved
0.6373	Remote Similarity	NPD6617	Approved
0.6373	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6354	Remote Similarity	NPD7639	Approved
0.6354	Remote Similarity	NPD7640	Approved
0.6354	Remote Similarity	NPD6404	Discontinued
0.6344	Remote Similarity	NPD7748	Approved
0.6338	Remote Similarity	NPD342	Phase 1
0.6337	Remote Similarity	NPD6012	Approved
0.6337	Remote Similarity	NPD6014	Approved
0.6337	Remote Similarity	NPD6373	Approved
0.6337	Remote Similarity	NPD6013	Approved
0.6337	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6882	Approved
0.6311	Remote Similarity	NPD8297	Approved
0.6304	Remote Similarity	NPD7637	Suspended
0.6304	Remote Similarity	NPD8034	Phase 2
0.6304	Remote Similarity	NPD8035	Phase 2
0.63	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD5169	Approved
0.6275	Remote Similarity	NPD5247	Approved
0.6275	Remote Similarity	NPD5250	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