NPASS Compound

Structure

NPC309310 OpenBabel07101718282D 30 31 0 0 1 0 0 0 0 0999 V2000 -9.4673 -2.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6637 -3.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7602 -2.2412 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 -4.3301 -1.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 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 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 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 0.0000 -0.0000 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 1 8 2 0 0 0 0 2 16 2 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 17 2 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 18 17 1 6 0 0 0 19 25 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 6 0 0 0 23 29 1 0 0 0 0 23 30 1 6 0 0 0 24 30 1 0 0 0 0 25 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.29
Volume:	457.248
LogP:	3.157
LogD:	3.302
LogS:	-4.326
# Rotatable Bonds:	7
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	5.101
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.835
MDCK Permeability:	1.9362760212970898e-05
Pgp-inhibitor:	0.495
Pgp-substrate:	0.789
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	90.36017608642578%
Volume Distribution (VD):	1.229
Pgp-substrate:	12.542440414428711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	1.061
Half-life (T1/2):	0.309

ADMET: Toxicity

hERG Blockers:	0.208
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.503
Carcinogencity:	0.064
Eye Corrosion:	0.027
Eye Irritation:	0.315
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC309310

Natural Product ID:	NPC309310
*Common Name:**	Fuscoside B
IUPAC Name:	(2S,3S,4R,5R)-2-[(3E,5E)-6-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-2-methylhepta-3,5-dien-2-yl]oxyoxane-3,4,5-triol
Synonyms:	Fuscoside B
Standard InCHIKey:	NUXJYWUAZCOBLA-RQWUNOCUSA-N
Standard InCHI:	InChI=1S/C25H40O5/c1-8-25(7)13-11-18(14-19(25)16(2)3)17(4)10-9-12-24(5,6)30-23-22(28)21(27)20(26)15-29-23/h8-10,12,18-23,26-28H,1-2,11,13-15H2,3-7H3/b12-9+,17-10+/t18-,19+,20+,21+,22-,23-,25-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)/C(=C/C=C/C(C)(C)O[C@H]1[C@H]([C@@H]([C@@H](CO1)O)O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1836649
PubChem CID:	56669207
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[21865038]
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22734800]
NPO27691	Eunicea fusca	Species	Plexauridae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	81.5	%	PMID[460262]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	52.0	%	PMID[460263]

☑ 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 NPC309310 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	202
0.1-0.2	1290
0.2-0.3	4893
0.3-0.4	12076
0.4-0.5	11970
0.5-0.6	7924
0.6-0.7	3741
0.7-0.8	579
0.8-0.85	17
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8989	High Similarity	NPC91654
0.8989	High Similarity	NPC474792
0.8989	High Similarity	NPC67398
0.8667	High Similarity	NPC302584
0.8602	High Similarity	NPC125551
0.8602	High Similarity	NPC91197
0.8602	High Similarity	NPC96597
0.8602	High Similarity	NPC309503
0.8602	High Similarity	NPC239547
0.8602	High Similarity	NPC155319
0.8438	Intermediate Similarity	NPC470571
0.8333	Intermediate Similarity	NPC285231
0.8333	Intermediate Similarity	NPC280991
0.8333	Intermediate Similarity	NPC21568
0.8298	Intermediate Similarity	NPC90583
0.8256	Intermediate Similarity	NPC100697
0.8242	Intermediate Similarity	NPC473058
0.8172	Intermediate Similarity	NPC474835
0.8152	Intermediate Similarity	NPC202886
0.8152	Intermediate Similarity	NPC261990
0.8152	Intermediate Similarity	NPC474249
0.8152	Intermediate Similarity	NPC159876
0.8144	Intermediate Similarity	NPC154127
0.8137	Intermediate Similarity	NPC65034
0.8137	Intermediate Similarity	NPC208189
0.8132	Intermediate Similarity	NPC248312
0.8125	Intermediate Similarity	NPC312325
0.81	Intermediate Similarity	NPC33053
0.809	Intermediate Similarity	NPC166279
0.8085	Intermediate Similarity	NPC305160
0.8065	Intermediate Similarity	NPC289361
0.8058	Intermediate Similarity	NPC231797
0.8043	Intermediate Similarity	NPC477748
0.8021	Intermediate Similarity	NPC240372
0.8021	Intermediate Similarity	NPC98112
0.798	Intermediate Similarity	NPC473124
0.798	Intermediate Similarity	NPC473123
0.7959	Intermediate Similarity	NPC267510
0.7941	Intermediate Similarity	NPC316974
0.7917	Intermediate Similarity	NPC207617
0.7912	Intermediate Similarity	NPC470836
0.79	Intermediate Similarity	NPC473127
0.79	Intermediate Similarity	NPC93352
0.79	Intermediate Similarity	NPC203354
0.79	Intermediate Similarity	NPC110656
0.7895	Intermediate Similarity	NPC25701
0.7895	Intermediate Similarity	NPC2003
0.7895	Intermediate Similarity	NPC211238
0.7872	Intermediate Similarity	NPC477749
0.7865	Intermediate Similarity	NPC20072
0.7864	Intermediate Similarity	NPC103627
0.7864	Intermediate Similarity	NPC191439
0.7864	Intermediate Similarity	NPC170974
0.7857	Intermediate Similarity	NPC64348
0.7857	Intermediate Similarity	NPC469942
0.7849	Intermediate Similarity	NPC470819
0.7843	Intermediate Similarity	NPC80210
0.7843	Intermediate Similarity	NPC128795
0.7843	Intermediate Similarity	NPC217921
0.7843	Intermediate Similarity	NPC135015
0.7843	Intermediate Similarity	NPC311223
0.7843	Intermediate Similarity	NPC38376
0.7843	Intermediate Similarity	NPC48548
0.7822	Intermediate Similarity	NPC239961
0.7822	Intermediate Similarity	NPC82251
0.7812	Intermediate Similarity	NPC230347
0.7812	Intermediate Similarity	NPC275310
0.7812	Intermediate Similarity	NPC286612
0.78	Intermediate Similarity	NPC134270
0.78	Intermediate Similarity	NPC99627
0.78	Intermediate Similarity	NPC471450
0.78	Intermediate Similarity	NPC473129
0.7791	Intermediate Similarity	NPC229655
0.7778	Intermediate Similarity	NPC470434
0.7778	Intermediate Similarity	NPC198992
0.7767	Intermediate Similarity	NPC285253
0.7767	Intermediate Similarity	NPC195116
0.7767	Intermediate Similarity	NPC473328
0.7767	Intermediate Similarity	NPC40728
0.7767	Intermediate Similarity	NPC472901
0.7767	Intermediate Similarity	NPC221110
0.7767	Intermediate Similarity	NPC180459
0.7767	Intermediate Similarity	NPC28844
0.7767	Intermediate Similarity	NPC473318
0.7766	Intermediate Similarity	NPC470817
0.7755	Intermediate Similarity	NPC198422
0.7755	Intermediate Similarity	NPC40182
0.7755	Intermediate Similarity	NPC158088
0.7745	Intermediate Similarity	NPC88013
0.7745	Intermediate Similarity	NPC281939
0.7745	Intermediate Similarity	NPC125423
0.7736	Intermediate Similarity	NPC475163
0.7727	Intermediate Similarity	NPC233295
0.7723	Intermediate Similarity	NPC57065
0.7723	Intermediate Similarity	NPC473207
0.7723	Intermediate Similarity	NPC201880
0.7723	Intermediate Similarity	NPC81567
0.7723	Intermediate Similarity	NPC54521
0.7723	Intermediate Similarity	NPC470321
0.7723	Intermediate Similarity	NPC109792
0.7723	Intermediate Similarity	NPC264867
0.7714	Intermediate Similarity	NPC470025
0.7714	Intermediate Similarity	NPC216595
0.7714	Intermediate Similarity	NPC328074
0.7714	Intermediate Similarity	NPC321272
0.7714	Intermediate Similarity	NPC317460
0.7714	Intermediate Similarity	NPC473567
0.7708	Intermediate Similarity	NPC96736
0.7708	Intermediate Similarity	NPC477927
0.7708	Intermediate Similarity	NPC178949
0.7708	Intermediate Similarity	NPC72817
0.77	Intermediate Similarity	NPC238397
0.77	Intermediate Similarity	NPC471363
0.77	Intermediate Similarity	NPC471889
0.7692	Intermediate Similarity	NPC119550
0.7692	Intermediate Similarity	NPC65155
0.7692	Intermediate Similarity	NPC83702
0.7692	Intermediate Similarity	NPC316708
0.7653	Intermediate Similarity	NPC473890
0.7653	Intermediate Similarity	NPC243728
0.7653	Intermediate Similarity	NPC26307
0.7647	Intermediate Similarity	NPC470767
0.7647	Intermediate Similarity	NPC472900
0.7647	Intermediate Similarity	NPC252296
0.7647	Intermediate Similarity	NPC472899
0.7647	Intermediate Similarity	NPC472898
0.7647	Intermediate Similarity	NPC470763
0.7647	Intermediate Similarity	NPC218158
0.7642	Intermediate Similarity	NPC470027
0.764	Intermediate Similarity	NPC190008
0.764	Intermediate Similarity	NPC474592
0.7629	Intermediate Similarity	NPC13924
0.7624	Intermediate Similarity	NPC162354
0.7624	Intermediate Similarity	NPC471888
0.7624	Intermediate Similarity	NPC7644
0.7624	Intermediate Similarity	NPC7613
0.7624	Intermediate Similarity	NPC127933
0.7624	Intermediate Similarity	NPC471886
0.7624	Intermediate Similarity	NPC475889
0.7624	Intermediate Similarity	NPC151516
0.7624	Intermediate Similarity	NPC471887
0.7624	Intermediate Similarity	NPC471885
0.7619	Intermediate Similarity	NPC470026
0.7619	Intermediate Similarity	NPC473021
0.7619	Intermediate Similarity	NPC472987
0.7619	Intermediate Similarity	NPC157474
0.7619	Intermediate Similarity	NPC17791
0.7619	Intermediate Similarity	NPC110494
0.7609	Intermediate Similarity	NPC119001
0.7609	Intermediate Similarity	NPC477747
0.7609	Intermediate Similarity	NPC477746
0.76	Intermediate Similarity	NPC47566
0.76	Intermediate Similarity	NPC88000
0.76	Intermediate Similarity	NPC472023
0.76	Intermediate Similarity	NPC160734
0.76	Intermediate Similarity	NPC21064
0.76	Intermediate Similarity	NPC129372
0.76	Intermediate Similarity	NPC121072
0.76	Intermediate Similarity	NPC4831
0.76	Intermediate Similarity	NPC309425
0.7596	Intermediate Similarity	NPC206618
0.7596	Intermediate Similarity	NPC250089
0.7596	Intermediate Similarity	NPC14630
0.7596	Intermediate Similarity	NPC157530
0.7582	Intermediate Similarity	NPC49208
0.7582	Intermediate Similarity	NPC23748
0.7579	Intermediate Similarity	NPC469403
0.7576	Intermediate Similarity	NPC280825
0.7576	Intermediate Similarity	NPC216260
0.7576	Intermediate Similarity	NPC81483
0.7576	Intermediate Similarity	NPC234287
0.7576	Intermediate Similarity	NPC5358
0.7576	Intermediate Similarity	NPC61630
0.7576	Intermediate Similarity	NPC307517
0.7576	Intermediate Similarity	NPC169468
0.7573	Intermediate Similarity	NPC257964
0.7573	Intermediate Similarity	NPC184512
0.7573	Intermediate Similarity	NPC231340
0.7573	Intermediate Similarity	NPC472390
0.7573	Intermediate Similarity	NPC109376
0.7553	Intermediate Similarity	NPC474629
0.7549	Intermediate Similarity	NPC473734
0.7549	Intermediate Similarity	NPC470768
0.7549	Intermediate Similarity	NPC75608
0.7549	Intermediate Similarity	NPC230948
0.7547	Intermediate Similarity	NPC473125
0.7547	Intermediate Similarity	NPC476305
0.7547	Intermediate Similarity	NPC475354
0.7526	Intermediate Similarity	NPC469491
0.7526	Intermediate Similarity	NPC88507
0.7525	Intermediate Similarity	NPC154452
0.7525	Intermediate Similarity	NPC37207
0.7525	Intermediate Similarity	NPC471482
0.7525	Intermediate Similarity	NPC150463
0.7525	Intermediate Similarity	NPC214277
0.7525	Intermediate Similarity	NPC300399
0.7525	Intermediate Similarity	NPC136816
0.7525	Intermediate Similarity	NPC272015
0.7524	Intermediate Similarity	NPC177047
0.7523	Intermediate Similarity	NPC473828

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 NPC309310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1384
0.2-0.3	4133
0.3-0.4	2327
0.4-0.5	751
0.5-0.6	282
0.6-0.7	87
0.7-0.8	5
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
0.75	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD7503	Approved
0.7207	Intermediate Similarity	NPD7328	Approved
0.7207	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD7516	Approved
0.7083	Intermediate Similarity	NPD7524	Approved
0.708	Intermediate Similarity	NPD8294	Approved
0.708	Intermediate Similarity	NPD8377	Approved
0.7075	Intermediate Similarity	NPD6412	Phase 2
0.7059	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8296	Approved
0.7018	Intermediate Similarity	NPD8335	Approved
0.7018	Intermediate Similarity	NPD8380	Approved
0.7018	Intermediate Similarity	NPD8033	Approved
0.7018	Intermediate Similarity	NPD8379	Approved
0.7018	Intermediate Similarity	NPD8378	Approved
0.6947	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7514	Phase 3
0.6882	Remote Similarity	NPD7332	Phase 2
0.6842	Remote Similarity	NPD6695	Phase 3
0.678	Remote Similarity	NPD7507	Approved
0.6739	Remote Similarity	NPD6932	Approved
0.6724	Remote Similarity	NPD8516	Approved
0.6724	Remote Similarity	NPD8517	Approved
0.6724	Remote Similarity	NPD8515	Approved
0.6724	Remote Similarity	NPD8513	Phase 3
0.6703	Remote Similarity	NPD8264	Approved
0.67	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7637	Suspended
0.6632	Remote Similarity	NPD6902	Approved
0.663	Remote Similarity	NPD6933	Approved
0.6612	Remote Similarity	NPD7319	Approved
0.6604	Remote Similarity	NPD5344	Discontinued
0.6566	Remote Similarity	NPD7750	Discontinued
0.6559	Remote Similarity	NPD6925	Approved
0.6559	Remote Similarity	NPD5776	Phase 2
0.6535	Remote Similarity	NPD46	Approved
0.6535	Remote Similarity	NPD6698	Approved
0.6526	Remote Similarity	NPD6930	Phase 2
0.6526	Remote Similarity	NPD6931	Approved
0.6509	Remote Similarity	NPD6648	Approved
0.6486	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6898	Phase 1
0.6444	Remote Similarity	NPD7143	Approved
0.6444	Remote Similarity	NPD7144	Approved
0.6421	Remote Similarity	NPD6929	Approved
0.6421	Remote Similarity	NPD6683	Phase 2
0.6415	Remote Similarity	NPD7638	Approved
0.6415	Remote Similarity	NPD4225	Approved
0.6413	Remote Similarity	NPD6926	Approved
0.6413	Remote Similarity	NPD6924	Approved
0.6387	Remote Similarity	NPD5126	Approved
0.6387	Remote Similarity	NPD5125	Phase 3
0.6374	Remote Similarity	NPD7150	Approved
0.6374	Remote Similarity	NPD7152	Approved
0.6374	Remote Similarity	NPD7151	Approved
0.6372	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6640	Phase 3
0.6355	Remote Similarity	NPD7639	Approved
0.6355	Remote Similarity	NPD7640	Approved
0.6354	Remote Similarity	NPD7525	Registered
0.6333	Remote Similarity	NPD6923	Approved
0.6333	Remote Similarity	NPD6922	Approved
0.6311	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD7087	Discontinued
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6370	Approved
0.62	Remote Similarity	NPD6893	Approved
0.6198	Remote Similarity	NPD8328	Phase 3
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7509	Discontinued
0.6179	Remote Similarity	NPD8074	Phase 3
0.6154	Remote Similarity	NPD6411	Approved
0.6136	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4732	Discontinued
0.6117	Remote Similarity	NPD6051	Approved
0.6102	Remote Similarity	NPD7115	Discovery
0.6102	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8451	Approved
0.6095	Remote Similarity	NPD5778	Approved
0.6095	Remote Similarity	NPD5779	Approved
0.6092	Remote Similarity	NPD368	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6066	Remote Similarity	NPD7830	Approved
0.6066	Remote Similarity	NPD7829	Approved
0.6064	Remote Similarity	NPD1810	Approved
0.6064	Remote Similarity	NPD1811	Approved
0.6058	Remote Similarity	NPD7136	Phase 2
0.6058	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3168	Discontinued
0.6048	Remote Similarity	NPD8448	Approved
0.6033	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD6942	Approved
0.6	Remote Similarity	NPD7339	Approved
0.5962	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6059	Approved
0.5943	Remote Similarity	NPD8171	Discontinued
0.5938	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7839	Suspended
0.5922	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8293	Discontinued
0.5906	Remote Similarity	NPD8391	Approved
0.5906	Remote Similarity	NPD8390	Approved
0.5906	Remote Similarity	NPD8392	Approved
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD6016	Approved
0.5897	Remote Similarity	NPD6882	Approved
0.5887	Remote Similarity	NPD8342	Approved
0.5887	Remote Similarity	NPD8341	Approved
0.5887	Remote Similarity	NPD7492	Approved
0.5887	Remote Similarity	NPD8340	Approved
0.5887	Remote Similarity	NPD8299	Approved
0.5882	Remote Similarity	NPD4219	Approved
0.5862	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6371	Approved
0.5856	Remote Similarity	NPD4159	Approved
0.5854	Remote Similarity	NPD5988	Approved
0.584	Remote Similarity	NPD6616	Approved
0.5833	Remote Similarity	NPD8039	Approved
0.5833	Remote Similarity	NPD6009	Approved
0.582	Remote Similarity	NPD7741	Discontinued
0.5814	Remote Similarity	NPD8449	Approved
0.5806	Remote Similarity	NPD6067	Discontinued
0.5804	Remote Similarity	NPD7632	Discontinued
0.5794	Remote Similarity	NPD7078	Approved
0.5794	Remote Similarity	NPD6399	Phase 3
0.5785	Remote Similarity	NPD7641	Discontinued
0.578	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8450	Suspended
0.5766	Remote Similarity	NPD6674	Discontinued
0.5763	Remote Similarity	NPD6053	Discontinued
0.5763	Remote Similarity	NPD8297	Approved
0.5758	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD2687	Approved
0.5745	Remote Similarity	NPD2254	Approved
0.5745	Remote Similarity	NPD2686	Approved
0.5743	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4784	Approved
0.5729	Remote Similarity	NPD4785	Approved
0.5728	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6084	Phase 2
0.5727	Remote Similarity	NPD6083	Phase 2
0.5725	Remote Similarity	NPD7625	Phase 1
0.5714	Remote Similarity	NPD4632	Approved
0.57	Remote Similarity	NPD4820	Approved
0.57	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4819	Approved
0.57	Remote Similarity	NPD4821	Approved
0.57	Remote Similarity	NPD4822	Approved
0.57	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6319	Approved
0.569	Remote Similarity	NPD6899	Approved
0.569	Remote Similarity	NPD6881	Approved
0.5684	Remote Similarity	NPD4243	Approved
0.568	Remote Similarity	NPD7642	Approved
0.5657	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD7128	Approved
0.5652	Remote Similarity	NPD5357	Phase 1
0.5652	Remote Similarity	NPD5739	Approved
0.5652	Remote Similarity	NPD6675	Approved
0.5652	Remote Similarity	NPD6402	Approved
0.5645	Remote Similarity	NPD6921	Approved
0.5631	Remote Similarity	NPD4786	Approved
0.5619	Remote Similarity	NPD4250	Approved
0.5619	Remote Similarity	NPD4251	Approved
0.5618	Remote Similarity	NPD1145	Discontinued
0.5615	Remote Similarity	NPD7260	Phase 2
0.5603	Remote Similarity	NPD5697	Approved
0.5603	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5954	Clinical (unspecified phase)

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