NPASS Compound

Structure

NPC475384 OpenBabel07101718322D 49 48 0 0 1 0 0 0 0 0999 V2000 -18.1865 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 14.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 5.1962 -2.0000 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 0.0000 C 0 0 3 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 10.3923 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 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 3 3 0 0 0 0 2 4 3 0 0 0 0 3 5 1 0 0 0 0 4 44 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 0 0 0 0 29 34 1 0 0 0 0 30 35 1 0 0 0 0 31 36 1 0 0 0 0 32 37 1 0 0 0 0 33 38 1 0 0 0 0 34 39 2 0 0 0 0 35 40 1 0 0 0 0 36 41 2 0 0 0 0 37 42 3 0 0 0 0 38 43 3 0 0 0 0 39 44 1 0 0 0 0 40 45 1 0 0 0 0 41 45 1 0 0 0 0 42 46 1 0 0 0 0 43 46 1 0 0 0 0 44 47 1 1 0 0 0 45 48 1 0 0 0 0 46 49 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	670.53
Volume:	798.905
LogP:	10.061
LogD:	4.956
LogS:	-2.168
# Rotatable Bonds:	31
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.039
Synthetic Accessibility Score:	4.696
Fsp3:	0.652
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.297
MDCK Permeability:	4.4803787204728e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.988
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	103.80855560302734%
Volume Distribution (VD):	0.426
Pgp-substrate:	0.3130571246147156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.535
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	2.989
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.394
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.993
Carcinogencity:	0.032
Eye Corrosion:	0.013
Eye Irritation:	0.946
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC475384

Natural Product ID:	NPC475384
*Common Name:**	Petrocortyne H
IUPAC Name:	(3R,4E,14R,21Z,26E,43Z)-hexatetraconta-4,21,26,43-tetraen-1,12,15,45-tetrayne-3,14,28-triol
Synonyms:	Petrocortyne H
Standard InCHIKey:	QGGNXNCVFAAWBQ-GCXPQEBYSA-N
Standard InCHI:	InChI=1S/C46H70O3/c1-3-5-6-7-8-9-10-11-12-13-14-16-19-25-30-35-40-45(48)41-36-31-26-20-17-15-18-21-27-32-37-42-46(49)43-38-33-28-23-22-24-29-34-39-44(47)4-2/h1-2,5-6,15,17,34,36,39,41,44-49H,7-14,16,18-33,35,40H2/b6-5-,17-15-,39-34+,41-36+/t44-,45?,46-/m0/s1
SMILES:	C#C/C=CCCCCCCCCCCCCCCC(/C=C/CCC/C=CCCCCC#C[C@@H](C#CCCCCCC/C=C/[C@H](C#C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504635
PubChem CID:	10580326
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514299]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21534590]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784165]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	11000.0	nM	PMID[493741]
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Inhibition	=	32.0	%	PMID[493741]

☑ 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 NPC475384 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	166
0.1-0.2	4010
0.2-0.3	19196
0.3-0.4	12552
0.4-0.5	5029
0.5-0.6	1345
0.6-0.7	249
0.7-0.8	64
0.8-0.85	20
0.85-0.9	30
0.9-0.95	15
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC161838
1.0	High Similarity	NPC470966
1.0	High Similarity	NPC470967
1.0	High Similarity	NPC470969
1.0	High Similarity	NPC471960
1.0	High Similarity	NPC470968
1.0	High Similarity	NPC473847
1.0	High Similarity	NPC477661
0.9811	High Similarity	NPC470970
0.9808	High Similarity	NPC477726
0.9808	High Similarity	NPC473910
0.9808	High Similarity	NPC475353
0.9808	High Similarity	NPC473735
0.9808	High Similarity	NPC477725
0.9808	High Similarity	NPC473721
0.9808	High Similarity	NPC473896
0.9808	High Similarity	NPC473725
0.9615	High Similarity	NPC473532
0.9423	High Similarity	NPC26102
0.9423	High Similarity	NPC477724
0.9423	High Similarity	NPC187361
0.9245	High Similarity	NPC49059
0.9245	High Similarity	NPC256209
0.9038	High Similarity	NPC471959
0.9038	High Similarity	NPC170776
0.9038	High Similarity	NPC256656
0.9038	High Similarity	NPC165447
0.9038	High Similarity	NPC224148
0.9038	High Similarity	NPC475477
0.9038	High Similarity	NPC89824
0.9038	High Similarity	NPC294278
0.9038	High Similarity	NPC329608
0.9038	High Similarity	NPC129263
0.9038	High Similarity	NPC477723
0.9038	High Similarity	NPC9273
0.9038	High Similarity	NPC76198
0.9038	High Similarity	NPC197272
0.8966	High Similarity	NPC470965
0.8846	High Similarity	NPC477727
0.8846	High Similarity	NPC199286
0.8846	High Similarity	NPC471281
0.8793	High Similarity	NPC475984
0.8704	High Similarity	NPC34577
0.8679	High Similarity	NPC55383
0.8679	High Similarity	NPC151782
0.8654	High Similarity	NPC471276
0.8654	High Similarity	NPC471275
0.8654	High Similarity	NPC125122
0.8654	High Similarity	NPC471280
0.8545	High Similarity	NPC110732
0.8545	High Similarity	NPC48058
0.8491	Intermediate Similarity	NPC72699
0.8491	Intermediate Similarity	NPC249670
0.8491	Intermediate Similarity	NPC473913
0.8491	Intermediate Similarity	NPC474642
0.8302	Intermediate Similarity	NPC31194
0.8302	Intermediate Similarity	NPC153538
0.8302	Intermediate Similarity	NPC85079
0.8302	Intermediate Similarity	NPC248884
0.8269	Intermediate Similarity	NPC124183
0.8269	Intermediate Similarity	NPC35141
0.8246	Intermediate Similarity	NPC311648
0.8246	Intermediate Similarity	NPC470964
0.8103	Intermediate Similarity	NPC48968
0.8103	Intermediate Similarity	NPC594
0.8095	Intermediate Similarity	NPC473752
0.807	Intermediate Similarity	NPC470963
0.807	Intermediate Similarity	NPC474513
0.807	Intermediate Similarity	NPC146551
0.807	Intermediate Similarity	NPC152668
0.8036	Intermediate Similarity	NPC474496
0.8033	Intermediate Similarity	NPC29697
0.8	Intermediate Similarity	NPC474495
0.8	Intermediate Similarity	NPC71053
0.8	Intermediate Similarity	NPC59408
0.8	Intermediate Similarity	NPC473672
0.8	Intermediate Similarity	NPC93639
0.7925	Intermediate Similarity	NPC19834
0.7925	Intermediate Similarity	NPC55063
0.7885	Intermediate Similarity	NPC101616
0.7869	Intermediate Similarity	NPC66460
0.7869	Intermediate Similarity	NPC271282
0.7869	Intermediate Similarity	NPC325929
0.7833	Intermediate Similarity	NPC473652
0.7818	Intermediate Similarity	NPC328784
0.7818	Intermediate Similarity	NPC291437
0.7759	Intermediate Similarity	NPC474644
0.7759	Intermediate Similarity	NPC471239
0.7736	Intermediate Similarity	NPC269074
0.7736	Intermediate Similarity	NPC76976
0.7636	Intermediate Similarity	NPC302310
0.7627	Intermediate Similarity	NPC474643
0.7627	Intermediate Similarity	NPC473865
0.7619	Intermediate Similarity	NPC470320
0.7619	Intermediate Similarity	NPC226592
0.7593	Intermediate Similarity	NPC157096
0.7581	Intermediate Similarity	NPC168407
0.7581	Intermediate Similarity	NPC477829
0.7547	Intermediate Similarity	NPC108195
0.7544	Intermediate Similarity	NPC142092
0.7541	Intermediate Similarity	NPC122239
0.75	Intermediate Similarity	NPC149668
0.75	Intermediate Similarity	NPC193975
0.7419	Intermediate Similarity	NPC471278
0.7377	Intermediate Similarity	NPC226848
0.7358	Intermediate Similarity	NPC252978
0.7273	Intermediate Similarity	NPC180575
0.7231	Intermediate Similarity	NPC136164
0.7231	Intermediate Similarity	NPC255863
0.7231	Intermediate Similarity	NPC308844
0.7231	Intermediate Similarity	NPC245947
0.7213	Intermediate Similarity	NPC474577
0.717	Intermediate Similarity	NPC304151
0.717	Intermediate Similarity	NPC46248
0.717	Intermediate Similarity	NPC249801
0.7167	Intermediate Similarity	NPC317899
0.7143	Intermediate Similarity	NPC327112
0.7115	Intermediate Similarity	NPC103236
0.7115	Intermediate Similarity	NPC27444
0.7115	Intermediate Similarity	NPC329762
0.7091	Intermediate Similarity	NPC276825
0.7091	Intermediate Similarity	NPC140501
0.7059	Intermediate Similarity	NPC103712
0.7059	Intermediate Similarity	NPC291196
0.7015	Intermediate Similarity	NPC26500
0.7015	Intermediate Similarity	NPC99619
0.6984	Remote Similarity	NPC475931
0.6984	Remote Similarity	NPC474267
0.6935	Remote Similarity	NPC212730
0.6935	Remote Similarity	NPC44542
0.6935	Remote Similarity	NPC265551
0.6935	Remote Similarity	NPC472445
0.6923	Remote Similarity	NPC471282
0.6897	Remote Similarity	NPC474460
0.6897	Remote Similarity	NPC473768
0.6885	Remote Similarity	NPC227135
0.6875	Remote Similarity	NPC243532
0.6833	Remote Similarity	NPC217188
0.6833	Remote Similarity	NPC284224
0.6833	Remote Similarity	NPC61177
0.6825	Remote Similarity	NPC181872
0.6825	Remote Similarity	NPC469373
0.6818	Remote Similarity	NPC300593
0.6812	Remote Similarity	NPC470436
0.6769	Remote Similarity	NPC201939
0.6769	Remote Similarity	NPC321838
0.6765	Remote Similarity	NPC73603
0.6765	Remote Similarity	NPC259299
0.6727	Remote Similarity	NPC116934
0.6724	Remote Similarity	NPC475153
0.6719	Remote Similarity	NPC222852
0.6716	Remote Similarity	NPC318420
0.6716	Remote Similarity	NPC326268
0.6667	Remote Similarity	NPC471279
0.6667	Remote Similarity	NPC477422
0.6667	Remote Similarity	NPC52012
0.6667	Remote Similarity	NPC35756
0.6667	Remote Similarity	NPC224532
0.6667	Remote Similarity	NPC471277
0.6667	Remote Similarity	NPC473508
0.6667	Remote Similarity	NPC288086
0.6667	Remote Similarity	NPC305698
0.6667	Remote Similarity	NPC55068
0.6667	Remote Similarity	NPC473705
0.6618	Remote Similarity	NPC267027
0.6615	Remote Similarity	NPC252851
0.6615	Remote Similarity	NPC240506
0.6615	Remote Similarity	NPC299730
0.6615	Remote Similarity	NPC154908
0.6615	Remote Similarity	NPC158368
0.6615	Remote Similarity	NPC226872
0.6615	Remote Similarity	NPC328311
0.6615	Remote Similarity	NPC99487
0.6613	Remote Similarity	NPC281590
0.6613	Remote Similarity	NPC329686
0.6613	Remote Similarity	NPC52264
0.6613	Remote Similarity	NPC54766
0.6604	Remote Similarity	NPC15934
0.6604	Remote Similarity	NPC306850
0.6571	Remote Similarity	NPC239373
0.6571	Remote Similarity	NPC74722
0.6571	Remote Similarity	NPC329989
0.6571	Remote Similarity	NPC304690
0.6571	Remote Similarity	NPC143396
0.6571	Remote Similarity	NPC471560
0.6567	Remote Similarity	NPC309300
0.6562	Remote Similarity	NPC23418
0.6562	Remote Similarity	NPC155025
0.6552	Remote Similarity	NPC471958
0.6545	Remote Similarity	NPC213538
0.6545	Remote Similarity	NPC256766
0.6545	Remote Similarity	NPC206906
0.6538	Remote Similarity	NPC216416
0.6528	Remote Similarity	NPC470435
0.6528	Remote Similarity	NPC329890
0.6522	Remote Similarity	NPC114651
0.6515	Remote Similarity	NPC113293
0.6515	Remote Similarity	NPC328776
0.6515	Remote Similarity	NPC225342
0.6515	Remote Similarity	NPC320305

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 NPC475384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	3947
0.2-0.3	3760
0.3-0.4	1050
0.4-0.5	160
0.5-0.6	64
0.6-0.7	8
0.7-0.8	0
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
0.7143	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4265	Approved
0.6667	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3197	Phase 1
0.6351	Remote Similarity	NPD8264	Approved
0.6349	Remote Similarity	NPD342	Phase 1
0.6329	Remote Similarity	NPD5332	Approved
0.6329	Remote Similarity	NPD5331	Approved
0.6286	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD368	Approved
0.619	Remote Similarity	NPD3196	Approved
0.619	Remote Similarity	NPD3194	Approved
0.619	Remote Similarity	NPD3195	Phase 2
0.619	Remote Similarity	NPD4266	Approved
0.6104	Remote Similarity	NPD4271	Approved
0.6104	Remote Similarity	NPD4268	Approved
0.6032	Remote Similarity	NPD3172	Approved
0.6027	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD4820	Approved
0.5949	Remote Similarity	NPD4821	Approved
0.5949	Remote Similarity	NPD4819	Approved
0.5949	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD4822	Approved
0.5897	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD4790	Discontinued
0.5875	Remote Similarity	NPD6898	Phase 1
0.5867	Remote Similarity	NPD4732	Discontinued
0.5833	Remote Similarity	NPD7750	Discontinued
0.5833	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4270	Approved
0.5802	Remote Similarity	NPD4269	Approved
0.5783	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4219	Approved
0.575	Remote Similarity	NPD7332	Phase 2
0.575	Remote Similarity	NPD4252	Approved
0.575	Remote Similarity	NPD7514	Phase 3
0.5732	Remote Similarity	NPD7154	Phase 3
0.5732	Remote Similarity	NPD5362	Discontinued
0.5714	Remote Similarity	NPD29	Approved
0.5714	Remote Similarity	NPD28	Approved
0.5696	Remote Similarity	NPD7145	Approved
0.5679	Remote Similarity	NPD6902	Approved
0.5667	Remote Similarity	NPD39	Approved
0.5645	Remote Similarity	NPD3173	Approved
0.5625	Remote Similarity	NPD6929	Approved
0.5625	Remote Similarity	NPD6683	Phase 2
0.56	Remote Similarity	NPD7143	Approved
0.56	Remote Similarity	NPD7144	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