NPASS Compound

Structure

NPC5985 OpenBabel07101718242D 29 33 0 0 1 0 0 0 0 0999 V2000 -4.1315 1.3894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5963 -0.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2784 2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8910 -0.7128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4373 1.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6231 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8226 2.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6231 -1.7128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0250 -0.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 -1.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 0.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4891 -0.2128 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 -3.3884 0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6231 0.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4891 -1.2128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8910 1.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4158 1.9563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8910 0.2872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0250 1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7570 -0.2128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1590 1.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3551 -1.7128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 5 10 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 2 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 27 1 0 0 0 0 16 29 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 26 1 0 0 0 0 20 28 1 1 0 0 0 21 7 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 26 1 1 0 0 0 24 27 1 1 0 0 0 25 29 1 0 0 0 0 26 4 1 1 0 0 0 27 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	283.12
Volume:	265.391
LogP:	-2.014
LogD:	-0.701
LogS:	-1.18
# Rotatable Bonds:	3
TPSA:	131.6
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	3.877
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.761
MDCK Permeability:	1.2633353435376193e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.542
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.285
Plasma Protein Binding (PPB):	49.62959289550781%
Volume Distribution (VD):	0.823
Pgp-substrate:	57.185943603515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.748
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	5.294
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.301
Drug-inuced Liver Injury (DILI):	0.628
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.087
Carcinogencity:	0.574
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.239

Download Data

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

Natural Product: NPC5985

Natural Product ID:	NPC5985
*Common Name:**	AQYVTAUQOOLBQC-ITDHJIIESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AQYVTAUQOOLBQC-ITDHJIIESA-N
Standard InCHI:	InChI=1S/C27H42O2/c1-17(2)5-10-25-18(3)22-8-9-24-21-7-6-19-15-20(28)11-13-26(19,4)23(21)12-14-27(22,24)16-29-25/h6,17,20-24,28H,5,7-16H2,1-4H3/t20-,21+,22+,23-,24-,26-,27-/m0/s1
SMILES:	CC(CCC1=C(C)[C@@H]2[C@@]3(CO1)CC[C@H]1[C@H]([C@@H]3CC2)CC=C2[C@]1(C)CC[C@@H](C2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517800
PubChem CID:	11211700
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
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[12542339]
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[15043442]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	GI50	=	3.52	ug.mL-1	PMID[538446]
NPT461	Cell Line	PANC-1	Homo sapiens	GI50	=	8.92	ug.mL-1	PMID[538446]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	=	6.91	ug.mL-1	PMID[538446]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	7.95	ug.mL-1	PMID[538446]

☑ 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 NPC5985 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	156
0.1-0.2	1321
0.2-0.3	5498
0.3-0.4	16185
0.4-0.5	7965
0.5-0.6	6022
0.6-0.7	4352
0.7-0.8	1002
0.8-0.85	114
0.85-0.9	61
0.9-0.95	20
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC321016
0.9211	High Similarity	NPC107059
0.9211	High Similarity	NPC321381
0.9103	High Similarity	NPC155924
0.9091	High Similarity	NPC155986
0.9091	High Similarity	NPC198968
0.9091	High Similarity	NPC318495
0.9079	High Similarity	NPC162742
0.9079	High Similarity	NPC136188
0.9079	High Similarity	NPC285893
0.9079	High Similarity	NPC22105
0.9079	High Similarity	NPC134847
0.9079	High Similarity	NPC230301
0.9079	High Similarity	NPC304309
0.9079	High Similarity	NPC28657
0.9079	High Similarity	NPC288035
0.8974	High Similarity	NPC474216
0.8974	High Similarity	NPC87604
0.8974	High Similarity	NPC477522
0.8974	High Similarity	NPC473943
0.8961	High Similarity	NPC240604
0.8961	High Similarity	NPC300324
0.8961	High Similarity	NPC113733
0.8875	High Similarity	NPC474731
0.8875	High Similarity	NPC474683
0.8875	High Similarity	NPC7505
0.8875	High Similarity	NPC82986
0.8875	High Similarity	NPC474752
0.8875	High Similarity	NPC474759
0.8861	High Similarity	NPC28862
0.8861	High Similarity	NPC47982
0.8861	High Similarity	NPC328714
0.8861	High Similarity	NPC109546
0.8861	High Similarity	NPC143182
0.8861	High Similarity	NPC84694
0.8861	High Similarity	NPC81306
0.8846	High Similarity	NPC34019
0.8831	High Similarity	NPC141071
0.8831	High Similarity	NPC471723
0.8831	High Similarity	NPC257347
0.875	High Similarity	NPC209944
0.875	High Similarity	NPC26117
0.875	High Similarity	NPC241290
0.875	High Similarity	NPC164840
0.875	High Similarity	NPC234193
0.8734	High Similarity	NPC307965
0.8734	High Similarity	NPC18603
0.8734	High Similarity	NPC76931
0.8734	High Similarity	NPC275910
0.8718	High Similarity	NPC129165
0.8718	High Similarity	NPC96319
0.8718	High Similarity	NPC189883
0.8718	High Similarity	NPC134330
0.8675	High Similarity	NPC474189
0.8675	High Similarity	NPC474349
0.8659	High Similarity	NPC475789
0.8642	High Similarity	NPC23852
0.8642	High Similarity	NPC264245
0.8642	High Similarity	NPC474531
0.8642	High Similarity	NPC47761
0.8642	High Similarity	NPC470383
0.8642	High Similarity	NPC209620
0.8625	High Similarity	NPC209430
0.8625	High Similarity	NPC1319
0.8625	High Similarity	NPC30986
0.8608	High Similarity	NPC214570
0.8571	High Similarity	NPC474970
0.8571	High Similarity	NPC474140
0.8571	High Similarity	NPC471799
0.8554	High Similarity	NPC209802
0.8554	High Similarity	NPC474047
0.8537	High Similarity	NPC1272
0.8537	High Similarity	NPC189972
0.8537	High Similarity	NPC50964
0.8537	High Similarity	NPC101462
0.8537	High Similarity	NPC248886
0.8537	High Similarity	NPC49964
0.8537	High Similarity	NPC470049
0.8537	High Similarity	NPC470614
0.8519	High Similarity	NPC236112
0.85	High Similarity	NPC477514
0.85	High Similarity	NPC244385
0.85	High Similarity	NPC167037
0.85	High Similarity	NPC6978
0.85	High Similarity	NPC138621
0.85	High Similarity	NPC285761
0.8481	Intermediate Similarity	NPC247325
0.8481	Intermediate Similarity	NPC202642
0.8481	Intermediate Similarity	NPC73875
0.8481	Intermediate Similarity	NPC470362
0.8481	Intermediate Similarity	NPC237460
0.8481	Intermediate Similarity	NPC244488
0.8481	Intermediate Similarity	NPC46160
0.8462	Intermediate Similarity	NPC471797
0.8452	Intermediate Similarity	NPC266511
0.8452	Intermediate Similarity	NPC274448
0.8452	Intermediate Similarity	NPC157257
0.8434	Intermediate Similarity	NPC317458
0.8434	Intermediate Similarity	NPC474634
0.8395	Intermediate Similarity	NPC80530
0.8395	Intermediate Similarity	NPC153987
0.8395	Intermediate Similarity	NPC44083
0.8395	Intermediate Similarity	NPC273410
0.8372	Intermediate Similarity	NPC471952
0.8354	Intermediate Similarity	NPC322353
0.8354	Intermediate Similarity	NPC121744
0.8354	Intermediate Similarity	NPC118508
0.8353	Intermediate Similarity	NPC125399
0.8353	Intermediate Similarity	NPC24277
0.8333	Intermediate Similarity	NPC221758
0.8333	Intermediate Similarity	NPC33913
0.8333	Intermediate Similarity	NPC470077
0.8333	Intermediate Similarity	NPC185568
0.8333	Intermediate Similarity	NPC205845
0.8333	Intermediate Similarity	NPC472265
0.8333	Intermediate Similarity	NPC124172
0.8333	Intermediate Similarity	NPC59453
0.8313	Intermediate Similarity	NPC20853
0.8313	Intermediate Similarity	NPC30166
0.8313	Intermediate Similarity	NPC201852
0.8293	Intermediate Similarity	NPC236237
0.8293	Intermediate Similarity	NPC322313
0.8293	Intermediate Similarity	NPC13554
0.8293	Intermediate Similarity	NPC102253
0.8289	Intermediate Similarity	NPC160209
0.8289	Intermediate Similarity	NPC208999
0.8272	Intermediate Similarity	NPC65897
0.8272	Intermediate Similarity	NPC22955
0.8272	Intermediate Similarity	NPC85346
0.8272	Intermediate Similarity	NPC474989
0.8272	Intermediate Similarity	NPC186191
0.8272	Intermediate Similarity	NPC302041
0.8272	Intermediate Similarity	NPC205455
0.8272	Intermediate Similarity	NPC470396
0.8272	Intermediate Similarity	NPC99168
0.8256	Intermediate Similarity	NPC149224
0.825	Intermediate Similarity	NPC106364
0.8228	Intermediate Similarity	NPC469593
0.8228	Intermediate Similarity	NPC100334
0.8228	Intermediate Similarity	NPC477138
0.8228	Intermediate Similarity	NPC243342
0.8228	Intermediate Similarity	NPC469533
0.8228	Intermediate Similarity	NPC469534
0.8228	Intermediate Similarity	NPC329090
0.8228	Intermediate Similarity	NPC27395
0.8205	Intermediate Similarity	NPC242001
0.8202	Intermediate Similarity	NPC235126
0.8202	Intermediate Similarity	NPC242419
0.8193	Intermediate Similarity	NPC116202
0.8193	Intermediate Similarity	NPC70927
0.8171	Intermediate Similarity	NPC472463
0.8171	Intermediate Similarity	NPC53744
0.8171	Intermediate Similarity	NPC291379
0.8161	Intermediate Similarity	NPC470542
0.8148	Intermediate Similarity	NPC157996
0.8148	Intermediate Similarity	NPC90979
0.8148	Intermediate Similarity	NPC40394
0.8148	Intermediate Similarity	NPC34177
0.8148	Intermediate Similarity	NPC471798
0.8148	Intermediate Similarity	NPC472805
0.8148	Intermediate Similarity	NPC101475
0.814	Intermediate Similarity	NPC145879
0.814	Intermediate Similarity	NPC51014
0.814	Intermediate Similarity	NPC474732
0.814	Intermediate Similarity	NPC152808
0.814	Intermediate Similarity	NPC474778
0.814	Intermediate Similarity	NPC6391
0.814	Intermediate Similarity	NPC94462
0.814	Intermediate Similarity	NPC474733
0.814	Intermediate Similarity	NPC31564
0.814	Intermediate Similarity	NPC293287
0.814	Intermediate Similarity	NPC155011
0.814	Intermediate Similarity	NPC477604
0.814	Intermediate Similarity	NPC261266
0.8125	Intermediate Similarity	NPC291503
0.8125	Intermediate Similarity	NPC471468
0.8125	Intermediate Similarity	NPC240235
0.8125	Intermediate Similarity	NPC231256
0.8125	Intermediate Similarity	NPC319090
0.8125	Intermediate Similarity	NPC212879
0.8125	Intermediate Similarity	NPC178383
0.8125	Intermediate Similarity	NPC104387
0.8125	Intermediate Similarity	NPC477923
0.8125	Intermediate Similarity	NPC328104
0.8125	Intermediate Similarity	NPC66566
0.8118	Intermediate Similarity	NPC478102
0.8118	Intermediate Similarity	NPC238485
0.8101	Intermediate Similarity	NPC201373
0.8101	Intermediate Similarity	NPC182717
0.8095	Intermediate Similarity	NPC87489
0.8095	Intermediate Similarity	NPC151519
0.8095	Intermediate Similarity	NPC202389
0.8095	Intermediate Similarity	NPC218616
0.8095	Intermediate Similarity	NPC296701
0.809	Intermediate Similarity	NPC471453
0.809	Intermediate Similarity	NPC234335
0.8077	Intermediate Similarity	NPC475728
0.8077	Intermediate Similarity	NPC145498
0.8068	Intermediate Similarity	NPC105495
0.8049	Intermediate Similarity	NPC476314

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 NPC5985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1494
0.2-0.3	4278
0.3-0.4	2296
0.4-0.5	495
0.5-0.6	174
0.6-0.7	180
0.7-0.8	62
0.8-0.85	15
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9079	High Similarity	NPD7339	Approved
0.9079	High Similarity	NPD6942	Approved
0.8718	High Similarity	NPD3701	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4786	Approved
0.8293	Intermediate Similarity	NPD7525	Registered
0.8228	Intermediate Similarity	NPD6926	Approved
0.8228	Intermediate Similarity	NPD6924	Approved
0.8171	Intermediate Similarity	NPD7645	Phase 2
0.8095	Intermediate Similarity	NPD3667	Approved
0.8025	Intermediate Similarity	NPD6933	Approved
0.8	Intermediate Similarity	NPD4785	Approved
0.8	Intermediate Similarity	NPD4784	Approved
0.7975	Intermediate Similarity	NPD7150	Approved
0.7975	Intermediate Similarity	NPD7152	Approved
0.7975	Intermediate Similarity	NPD4243	Approved
0.7975	Intermediate Similarity	NPD7151	Approved
0.7949	Intermediate Similarity	NPD6923	Approved
0.7949	Intermediate Similarity	NPD6922	Approved
0.7848	Intermediate Similarity	NPD7143	Approved
0.7848	Intermediate Similarity	NPD7144	Approved
0.7841	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6399	Phase 3
0.7791	Intermediate Similarity	NPD6695	Phase 3
0.7738	Intermediate Similarity	NPD6929	Approved
0.7701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5328	Approved
0.7647	Intermediate Similarity	NPD6930	Phase 2
0.7647	Intermediate Similarity	NPD6931	Approved
0.7647	Intermediate Similarity	NPD4748	Discontinued
0.7528	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD6925	Approved
0.75	Intermediate Similarity	NPD6932	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD5776	Phase 2
0.747	Intermediate Similarity	NPD4190	Phase 3
0.747	Intermediate Similarity	NPD5275	Approved
0.7444	Intermediate Similarity	NPD7750	Discontinued
0.7444	Intermediate Similarity	NPD7524	Approved
0.7442	Intermediate Similarity	NPD7509	Discontinued
0.7412	Intermediate Similarity	NPD7145	Approved
0.7326	Intermediate Similarity	NPD6683	Phase 2
0.7326	Intermediate Similarity	NPD4195	Approved
0.7303	Intermediate Similarity	NPD3668	Phase 3
0.7241	Intermediate Similarity	NPD7514	Phase 3
0.7234	Intermediate Similarity	NPD4202	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6893	Approved
0.7209	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6902	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD5330	Approved
0.7128	Intermediate Similarity	NPD7087	Discontinued
0.7113	Intermediate Similarity	NPD6083	Phase 2
0.7113	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7097	Intermediate Similarity	NPD6051	Approved
0.7079	Intermediate Similarity	NPD4223	Phase 3
0.7079	Intermediate Similarity	NPD4221	Approved
0.7059	Intermediate Similarity	NPD8264	Approved
0.7045	Intermediate Similarity	NPD7332	Phase 2
0.7041	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD5329	Approved
0.701	Intermediate Similarity	NPD4697	Phase 3
0.701	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5221	Approved
0.701	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD4788	Approved
0.6989	Remote Similarity	NPD5737	Approved
0.6989	Remote Similarity	NPD6672	Approved
0.6989	Remote Similarity	NPD6903	Approved
0.6979	Remote Similarity	NPD7748	Approved
0.697	Remote Similarity	NPD7639	Approved
0.697	Remote Similarity	NPD7640	Approved
0.6966	Remote Similarity	NPD6898	Phase 1
0.6961	Remote Similarity	NPD5739	Approved
0.6961	Remote Similarity	NPD7128	Approved
0.6961	Remote Similarity	NPD6675	Approved
0.6961	Remote Similarity	NPD6402	Approved
0.6947	Remote Similarity	NPD8034	Phase 2
0.6947	Remote Similarity	NPD8035	Phase 2
0.6947	Remote Similarity	NPD7515	Phase 2
0.6939	Remote Similarity	NPD5173	Approved
0.6939	Remote Similarity	NPD4755	Approved
0.6923	Remote Similarity	NPD4197	Approved
0.6827	Remote Similarity	NPD7320	Approved
0.6827	Remote Similarity	NPD6899	Approved
0.6827	Remote Similarity	NPD6881	Approved
0.6818	Remote Similarity	NPD3617	Approved
0.68	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD4696	Approved
0.68	Remote Similarity	NPD5286	Approved
0.68	Remote Similarity	NPD4700	Approved
0.6789	Remote Similarity	NPD7115	Discovery
0.6774	Remote Similarity	NPD4138	Approved
0.6774	Remote Similarity	NPD4688	Approved
0.6774	Remote Similarity	NPD6098	Approved
0.6774	Remote Similarity	NPD4689	Approved
0.6774	Remote Similarity	NPD5205	Approved
0.6774	Remote Similarity	NPD4693	Phase 3
0.6774	Remote Similarity	NPD4690	Approved
0.6771	Remote Similarity	NPD7637	Suspended
0.6768	Remote Similarity	NPD7902	Approved
0.6762	Remote Similarity	NPD6373	Approved
0.6762	Remote Similarity	NPD6372	Approved
0.6735	Remote Similarity	NPD5210	Approved
0.6735	Remote Similarity	NPD5695	Phase 3
0.6735	Remote Similarity	NPD4629	Approved
0.6733	Remote Similarity	NPD4159	Approved
0.6733	Remote Similarity	NPD5223	Approved
0.6731	Remote Similarity	NPD5701	Approved
0.6731	Remote Similarity	NPD5697	Approved
0.6731	Remote Similarity	NPD6412	Phase 2
0.67	Remote Similarity	NPD5696	Approved
0.67	Remote Similarity	NPD5290	Discontinued
0.6698	Remote Similarity	NPD6883	Approved
0.6698	Remote Similarity	NPD7290	Approved
0.6698	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD8130	Phase 1
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD6869	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6847	Approved
0.6632	Remote Similarity	NPD4723	Approved
0.6632	Remote Similarity	NPD4722	Approved
0.6604	Remote Similarity	NPD6012	Approved
0.6604	Remote Similarity	NPD6014	Approved
0.6604	Remote Similarity	NPD6013	Approved
0.6602	Remote Similarity	NPD5175	Approved
0.6602	Remote Similarity	NPD5174	Approved
0.6602	Remote Similarity	NPD4754	Approved
0.6596	Remote Similarity	NPD5280	Approved
0.6596	Remote Similarity	NPD5690	Phase 2
0.6596	Remote Similarity	NPD4694	Approved
0.6588	Remote Similarity	NPD4787	Phase 1
0.6574	Remote Similarity	NPD8297	Approved
0.6574	Remote Similarity	NPD6882	Approved
0.6562	Remote Similarity	NPD6080	Approved
0.6562	Remote Similarity	NPD6904	Approved
0.6562	Remote Similarity	NPD6673	Approved
0.6549	Remote Similarity	NPD7503	Approved
0.6538	Remote Similarity	NPD5141	Approved
0.6512	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6928	Phase 2
0.6476	Remote Similarity	NPD4767	Approved
0.6476	Remote Similarity	NPD4768	Approved
0.6465	Remote Similarity	NPD7900	Approved
0.6465	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5208	Approved
0.6429	Remote Similarity	NPD6411	Approved
0.6422	Remote Similarity	NPD6053	Discontinued
0.6421	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4692	Approved
0.6413	Remote Similarity	NPD4139	Approved
0.64	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6868	Approved
0.6395	Remote Similarity	NPD4747	Approved
0.6392	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4730	Approved
0.6355	Remote Similarity	NPD5128	Approved
0.6355	Remote Similarity	NPD5168	Approved
0.6355	Remote Similarity	NPD4729	Approved
0.6346	Remote Similarity	NPD7632	Discontinued
0.6327	Remote Similarity	NPD7136	Phase 2
0.6321	Remote Similarity	NPD6008	Approved
0.63	Remote Similarity	NPD5707	Approved
0.6283	Remote Similarity	NPD6335	Approved
0.6283	Remote Similarity	NPD7328	Approved
0.6283	Remote Similarity	NPD7327	Approved
0.6279	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4137	Phase 3
0.6263	Remote Similarity	NPD5281	Approved
0.6263	Remote Similarity	NPD5284	Approved
0.6263	Remote Similarity	NPD6050	Approved
0.6263	Remote Similarity	NPD5693	Phase 1
0.6261	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD6274	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