NPASS Compound

Structure

NPC255174 OpenBabel07101718312D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 0.6340 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 -3.4641 3.0000 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 -3.4641 -0.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 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 -0.0000 -0.0000 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 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 1 0 0 0 17 24 2 0 0 0 0 18 21 1 0 0 0 0 18 22 1 1 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 22 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	5.57
LogD:	3.423
LogS:	-3.832
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	3.994
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	1.698122468951624e-05
Pgp-inhibitor:	0.637
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.649

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	98.72314453125%
Volume Distribution (VD):	2.942
Pgp-substrate:	1.3918986320495605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.178
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.342
CYP2C19-substrate:	0.43
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.383
CYP2D6-substrate:	0.327
CYP3A4-inhibitor:	0.273
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	11.193
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.171
Rat Oral Acute Toxicity:	0.211
Maximum Recommended Daily Dose:	0.43
Skin Sensitization:	0.902
Carcinogencity:	0.488
Eye Corrosion:	0.024
Eye Irritation:	0.903
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC255174

Natural Product ID:	NPC255174
*Common Name:**	Tauranin
IUPAC Name:	2-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-3-hydroxy-5-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione
Synonyms:	tauranin
Standard InCHIKey:	KNEPVLLGXUSFJS-SGXKBVARSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13-6-7-18-21(2,3)8-5-9-22(18,4)16(13)11-15-17(24)10-14(12-23)19(25)20(15)26/h10,16,18,23,26H,1,5-9,11-12H2,2-4H3/t16-,18-,22+/m0/s1
SMILES:	C=C1CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1CC1=C(C(=O)C(=CC1=O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255318
PubChem CID:	44448194
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO15998	Phyllosticta spinarum	Species	Phyllostictaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18247573]
NPO15998	Phyllosticta spinarum	Species	Phyllostictaceae	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
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	4300.0	nM	PMID[546169]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1500.0	nM	PMID[546169]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	1800.0	nM	PMID[546169]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	2800.0	nM	PMID[546169]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3500.0	nM	PMID[546169]

☑ 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 NPC255174 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	179
0.1-0.2	1197
0.2-0.3	5148
0.3-0.4	11784
0.4-0.5	12775
0.5-0.6	6978
0.6-0.7	3861
0.7-0.8	751
0.8-0.85	21
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8452	Intermediate Similarity	NPC103486
0.8391	Intermediate Similarity	NPC220930
0.8391	Intermediate Similarity	NPC272039
0.8372	Intermediate Similarity	NPC476426
0.8333	Intermediate Similarity	NPC116797
0.8295	Intermediate Similarity	NPC53454
0.8276	Intermediate Similarity	NPC470955
0.8256	Intermediate Similarity	NPC476412
0.8193	Intermediate Similarity	NPC475994
0.8171	Intermediate Similarity	NPC1254
0.8161	Intermediate Similarity	NPC6185
0.8161	Intermediate Similarity	NPC241512
0.8125	Intermediate Similarity	NPC131366
0.8118	Intermediate Similarity	NPC55869
0.8118	Intermediate Similarity	NPC99308
0.8095	Intermediate Similarity	NPC27817
0.809	Intermediate Similarity	NPC471791
0.809	Intermediate Similarity	NPC58271
0.809	Intermediate Similarity	NPC471793
0.8068	Intermediate Similarity	NPC194417
0.8068	Intermediate Similarity	NPC472974
0.8043	Intermediate Similarity	NPC474882
0.8022	Intermediate Similarity	NPC172101
0.8	Intermediate Similarity	NPC2482
0.8	Intermediate Similarity	NPC108955
0.7976	Intermediate Similarity	NPC478122
0.7976	Intermediate Similarity	NPC62336
0.7955	Intermediate Similarity	NPC132228
0.7955	Intermediate Similarity	NPC32037
0.7955	Intermediate Similarity	NPC70685
0.7955	Intermediate Similarity	NPC263997
0.7955	Intermediate Similarity	NPC8518
0.7955	Intermediate Similarity	NPC474680
0.7952	Intermediate Similarity	NPC263582
0.7952	Intermediate Similarity	NPC110725
0.7931	Intermediate Similarity	NPC105803
0.7917	Intermediate Similarity	NPC470184
0.7907	Intermediate Similarity	NPC14151
0.7907	Intermediate Similarity	NPC121984
0.7889	Intermediate Similarity	NPC307298
0.7882	Intermediate Similarity	NPC19900
0.7882	Intermediate Similarity	NPC308038
0.7865	Intermediate Similarity	NPC472986
0.7865	Intermediate Similarity	NPC472985
0.7865	Intermediate Similarity	NPC94666
0.7849	Intermediate Similarity	NPC472976
0.7849	Intermediate Similarity	NPC472977
0.7849	Intermediate Similarity	NPC23170
0.7841	Intermediate Similarity	NPC237712
0.7826	Intermediate Similarity	NPC472978
0.7826	Intermediate Similarity	NPC23217
0.7826	Intermediate Similarity	NPC26865
0.7802	Intermediate Similarity	NPC472983
0.7802	Intermediate Similarity	NPC472973
0.7802	Intermediate Similarity	NPC472477
0.7802	Intermediate Similarity	NPC472475
0.7791	Intermediate Similarity	NPC45495
0.7791	Intermediate Similarity	NPC157895
0.7791	Intermediate Similarity	NPC104120
0.7791	Intermediate Similarity	NPC472478
0.7791	Intermediate Similarity	NPC148685
0.7766	Intermediate Similarity	NPC280725
0.7753	Intermediate Similarity	NPC474853
0.7753	Intermediate Similarity	NPC79573
0.7753	Intermediate Similarity	NPC33881
0.7753	Intermediate Similarity	NPC179006
0.7753	Intermediate Similarity	NPC472931
0.7753	Intermediate Similarity	NPC472940
0.7742	Intermediate Similarity	NPC476416
0.7742	Intermediate Similarity	NPC109305
0.7742	Intermediate Similarity	NPC474736
0.7742	Intermediate Similarity	NPC474807
0.7738	Intermediate Similarity	NPC26504
0.7738	Intermediate Similarity	NPC470525
0.7727	Intermediate Similarity	NPC41539
0.7717	Intermediate Similarity	NPC48010
0.7717	Intermediate Similarity	NPC113393
0.7717	Intermediate Similarity	NPC475823
0.7717	Intermediate Similarity	NPC474209
0.7717	Intermediate Similarity	NPC51486
0.7711	Intermediate Similarity	NPC147438
0.7711	Intermediate Similarity	NPC215050
0.7708	Intermediate Similarity	NPC316598
0.7701	Intermediate Similarity	NPC470034
0.7701	Intermediate Similarity	NPC475863
0.7701	Intermediate Similarity	NPC225515
0.7701	Intermediate Similarity	NPC6663
0.7692	Intermediate Similarity	NPC72397
0.7684	Intermediate Similarity	NPC29152
0.7683	Intermediate Similarity	NPC474884
0.7683	Intermediate Similarity	NPC133253
0.7683	Intermediate Similarity	NPC21944
0.7674	Intermediate Similarity	NPC7232
0.7667	Intermediate Similarity	NPC327115
0.7653	Intermediate Similarity	NPC87351
0.7647	Intermediate Similarity	NPC476811
0.7647	Intermediate Similarity	NPC74995
0.7634	Intermediate Similarity	NPC99380
0.7634	Intermediate Similarity	NPC73457
0.7634	Intermediate Similarity	NPC473998
0.7619	Intermediate Similarity	NPC476346
0.7614	Intermediate Similarity	NPC48362
0.7614	Intermediate Similarity	NPC472239
0.7614	Intermediate Similarity	NPC38796
0.7614	Intermediate Similarity	NPC93590
0.7614	Intermediate Similarity	NPC212083
0.7614	Intermediate Similarity	NPC472867
0.7614	Intermediate Similarity	NPC158411
0.7609	Intermediate Similarity	NPC473999
0.7609	Intermediate Similarity	NPC477973
0.7609	Intermediate Similarity	NPC474918
0.7609	Intermediate Similarity	NPC310010
0.7609	Intermediate Similarity	NPC326627
0.7609	Intermediate Similarity	NPC472676
0.7609	Intermediate Similarity	NPC309603
0.7609	Intermediate Similarity	NPC472688
0.7604	Intermediate Similarity	NPC471916
0.7604	Intermediate Similarity	NPC156546
0.7604	Intermediate Similarity	NPC208094
0.7604	Intermediate Similarity	NPC170131
0.759	Intermediate Similarity	NPC56747
0.759	Intermediate Similarity	NPC180015
0.759	Intermediate Similarity	NPC130016
0.759	Intermediate Similarity	NPC109576
0.7586	Intermediate Similarity	NPC287063
0.7582	Intermediate Similarity	NPC476409
0.7579	Intermediate Similarity	NPC209355
0.7576	Intermediate Similarity	NPC311612
0.7576	Intermediate Similarity	NPC95899
0.7576	Intermediate Similarity	NPC111323
0.7561	Intermediate Similarity	NPC286154
0.7558	Intermediate Similarity	NPC198240
0.7558	Intermediate Similarity	NPC30321
0.7558	Intermediate Similarity	NPC82635
0.7558	Intermediate Similarity	NPC189485
0.7556	Intermediate Similarity	NPC274724
0.7556	Intermediate Similarity	NPC469948
0.7556	Intermediate Similarity	NPC133652
0.7556	Intermediate Similarity	NPC471224
0.7553	Intermediate Similarity	NPC271652
0.7553	Intermediate Similarity	NPC211230
0.7549	Intermediate Similarity	NPC87335
0.7531	Intermediate Similarity	NPC155198
0.7529	Intermediate Similarity	NPC92080
0.7529	Intermediate Similarity	NPC19907
0.7528	Intermediate Similarity	NPC49019
0.7528	Intermediate Similarity	NPC297398
0.7528	Intermediate Similarity	NPC53733
0.7528	Intermediate Similarity	NPC258985
0.7527	Intermediate Similarity	NPC38952
0.7527	Intermediate Similarity	NPC230332
0.7527	Intermediate Similarity	NPC472476
0.7526	Intermediate Similarity	NPC478056
0.7526	Intermediate Similarity	NPC147954
0.7525	Intermediate Similarity	NPC472925
0.75	Intermediate Similarity	NPC278459
0.75	Intermediate Similarity	NPC1753
0.75	Intermediate Similarity	NPC48107
0.75	Intermediate Similarity	NPC189237
0.75	Intermediate Similarity	NPC44963
0.75	Intermediate Similarity	NPC4166
0.75	Intermediate Similarity	NPC474085
0.75	Intermediate Similarity	NPC117133
0.75	Intermediate Similarity	NPC474511
0.75	Intermediate Similarity	NPC184065
0.75	Intermediate Similarity	NPC471463
0.75	Intermediate Similarity	NPC472684
0.75	Intermediate Similarity	NPC90055
0.75	Intermediate Similarity	NPC104560
0.7474	Intermediate Similarity	NPC476415
0.7474	Intermediate Similarity	NPC245972
0.7474	Intermediate Similarity	NPC474328
0.7474	Intermediate Similarity	NPC196485
0.7474	Intermediate Similarity	NPC473162
0.7474	Intermediate Similarity	NPC78159
0.7474	Intermediate Similarity	NPC8993
0.7473	Intermediate Similarity	NPC82979
0.7473	Intermediate Similarity	NPC474778
0.7473	Intermediate Similarity	NPC145879
0.7473	Intermediate Similarity	NPC472479
0.7473	Intermediate Similarity	NPC474732
0.7473	Intermediate Similarity	NPC473226
0.7473	Intermediate Similarity	NPC51014
0.7473	Intermediate Similarity	NPC229717
0.7473	Intermediate Similarity	NPC31564
0.7473	Intermediate Similarity	NPC198761
0.7473	Intermediate Similarity	NPC20688
0.7473	Intermediate Similarity	NPC322159
0.7473	Intermediate Similarity	NPC474733
0.7471	Intermediate Similarity	NPC472490
0.7471	Intermediate Similarity	NPC192329
0.7471	Intermediate Similarity	NPC476177
0.7471	Intermediate Similarity	NPC170394
0.7471	Intermediate Similarity	NPC152061
0.7471	Intermediate Similarity	NPC281138
0.7449	Intermediate Similarity	NPC174314
0.7447	Intermediate Similarity	NPC475806
0.7447	Intermediate Similarity	NPC472814
0.7447	Intermediate Similarity	NPC168027
0.7447	Intermediate Similarity	NPC185936

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 NPC255174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1509
0.2-0.3	4035
0.3-0.4	2401
0.4-0.5	636
0.5-0.6	203
0.6-0.7	169
0.7-0.8	39
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8434	Intermediate Similarity	NPD4695	Discontinued
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7475	Intermediate Similarity	NPD5211	Phase 2
0.7473	Intermediate Similarity	NPD5279	Phase 3
0.7444	Intermediate Similarity	NPD3666	Approved
0.7444	Intermediate Similarity	NPD3665	Phase 1
0.7444	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD3667	Approved
0.7396	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD4629	Approved
0.7356	Intermediate Similarity	NPD3617	Approved
0.7349	Intermediate Similarity	NPD4691	Approved
0.7327	Intermediate Similarity	NPD5141	Approved
0.732	Intermediate Similarity	NPD5221	Approved
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4623	Approved
0.7283	Intermediate Similarity	NPD3618	Phase 1
0.7283	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4519	Discontinued
0.7273	Intermediate Similarity	NPD4696	Approved
0.7273	Intermediate Similarity	NPD5286	Approved
0.7273	Intermediate Similarity	NPD5285	Approved
0.7253	Intermediate Similarity	NPD4786	Approved
0.7253	Intermediate Similarity	NPD4197	Approved
0.7245	Intermediate Similarity	NPD5173	Approved
0.7245	Intermediate Similarity	NPD4755	Approved
0.7234	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4137	Phase 3
0.72	Intermediate Similarity	NPD5223	Approved
0.7191	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5329	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7143	Intermediate Similarity	NPD4747	Approved
0.7129	Intermediate Similarity	NPD5224	Approved
0.7129	Intermediate Similarity	NPD5226	Approved
0.7129	Intermediate Similarity	NPD4633	Approved
0.7129	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD4700	Approved
0.7097	Intermediate Similarity	NPD5690	Phase 2
0.7093	Intermediate Similarity	NPD4058	Approved
0.7083	Intermediate Similarity	NPD6079	Approved
0.7083	Intermediate Similarity	NPD7515	Phase 2
0.7071	Intermediate Similarity	NPD6084	Phase 2
0.7071	Intermediate Similarity	NPD6083	Phase 2
0.7059	Intermediate Similarity	NPD5174	Approved
0.7059	Intermediate Similarity	NPD5175	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7033	Intermediate Similarity	NPD4223	Phase 3
0.7033	Intermediate Similarity	NPD4221	Approved
0.701	Intermediate Similarity	NPD4202	Approved
0.6989	Remote Similarity	NPD1696	Phase 3
0.6981	Remote Similarity	NPD4634	Approved
0.6947	Remote Similarity	NPD6672	Approved
0.6947	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD4694	Approved
0.6915	Remote Similarity	NPD5280	Approved
0.6893	Remote Similarity	NPD4754	Approved
0.6882	Remote Similarity	NPD3668	Phase 3
0.6869	Remote Similarity	NPD5695	Phase 3
0.686	Remote Similarity	NPD5276	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6399	Phase 3
0.6832	Remote Similarity	NPD5696	Approved
0.6832	Remote Similarity	NPD4225	Approved
0.6809	Remote Similarity	NPD5363	Approved
0.6804	Remote Similarity	NPD5785	Approved
0.6792	Remote Similarity	NPD4729	Approved
0.6792	Remote Similarity	NPD5128	Approved
0.6792	Remote Similarity	NPD6011	Approved
0.6792	Remote Similarity	NPD6881	Approved
0.6792	Remote Similarity	NPD6899	Approved
0.6792	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD4788	Approved
0.6768	Remote Similarity	NPD5282	Discontinued
0.6768	Remote Similarity	NPD7748	Approved
0.6762	Remote Similarity	NPD5739	Approved
0.6762	Remote Similarity	NPD6675	Approved
0.6762	Remote Similarity	NPD4768	Approved
0.6762	Remote Similarity	NPD6402	Approved
0.6762	Remote Similarity	NPD7128	Approved
0.6762	Remote Similarity	NPD4767	Approved
0.6757	Remote Similarity	NPD7115	Discovery
0.6737	Remote Similarity	NPD5205	Approved
0.6737	Remote Similarity	NPD4688	Approved
0.6737	Remote Similarity	NPD4138	Approved
0.6737	Remote Similarity	NPD4693	Phase 3
0.6737	Remote Similarity	NPD4690	Approved
0.6737	Remote Similarity	NPD4689	Approved
0.6733	Remote Similarity	NPD7902	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6707	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4687	Approved
0.6705	Remote Similarity	NPD5733	Approved
0.6698	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6606	Remote Similarity	NPD6847	Approved
0.6606	Remote Similarity	NPD6869	Approved
0.6606	Remote Similarity	NPD5215	Approved
0.6606	Remote Similarity	NPD8130	Phase 1
0.6606	Remote Similarity	NPD6617	Approved
0.6606	Remote Similarity	NPD5216	Approved
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD5127	Approved
0.6606	Remote Similarity	NPD6649	Approved
0.6606	Remote Similarity	NPD5217	Approved
0.6593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6372	Approved
0.6574	Remote Similarity	NPD6373	Approved
0.6566	Remote Similarity	NPD5284	Approved
0.6566	Remote Similarity	NPD6411	Approved
0.6566	Remote Similarity	NPD5281	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6566	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD7521	Approved
0.6562	Remote Similarity	NPD6409	Approved
0.6562	Remote Similarity	NPD6684	Approved
0.6562	Remote Similarity	NPD7146	Approved
0.6562	Remote Similarity	NPD5330	Approved
0.6562	Remote Similarity	NPD7334	Approved
0.6545	Remote Similarity	NPD6882	Approved
0.6545	Remote Similarity	NPD8297	Approved
0.6531	Remote Similarity	NPD6904	Approved
0.6531	Remote Similarity	NPD6673	Approved
0.6531	Remote Similarity	NPD6080	Approved
0.6522	Remote Similarity	NPD4195	Approved
0.65	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD5779	Approved
0.6491	Remote Similarity	NPD4522	Approved
0.6489	Remote Similarity	NPD4270	Approved
0.6489	Remote Similarity	NPD4269	Approved
0.6486	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD6686	Approved
0.6476	Remote Similarity	NPD5091	Approved
0.6471	Remote Similarity	NPD3704	Approved
0.6455	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4252	Approved
0.6444	Remote Similarity	NPD8264	Approved
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6436	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7900	Approved
0.6435	Remote Similarity	NPD6319	Approved
0.6435	Remote Similarity	NPD6054	Approved
0.6429	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD5167	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6110	Phase 1
0.6389	Remote Similarity	NPD6412	Phase 2
0.6383	Remote Similarity	NPD8028	Phase 2
0.6379	Remote Similarity	NPD6015	Approved
0.6379	Remote Similarity	NPD6016	Approved
0.6374	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7638	Approved
0.6337	Remote Similarity	NPD5133	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.6325	Remote Similarity	NPD5988	Approved
0.6325	Remote Similarity	NPD6370	Approved
0.6316	Remote Similarity	NPD6009	Approved
0.6316	Remote Similarity	NPD6317	Approved
0.6311	Remote Similarity	NPD7614	Phase 1
0.63	Remote Similarity	NPD4096	Approved
0.63	Remote Similarity	NPD5692	Phase 3
0.6293	Remote Similarity	NPD6059	Approved
0.6279	Remote Similarity	NPD7331	Phase 2
0.6264	Remote Similarity	NPD6942	Approved
0.6264	Remote Similarity	NPD7339	Approved
0.6263	Remote Similarity	NPD4518	Approved
0.6261	Remote Similarity	NPD6314	Approved
0.6261	Remote Similarity	NPD6313	Approved
0.6261	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6050	Approved
0.6238	Remote Similarity	NPD5694	Approved
0.6237	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6868	Approved
0.6224	Remote Similarity	NPD6098	Approved
0.6224	Remote Similarity	NPD5786	Approved
0.622	Remote Similarity	NPD287	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