NPASS Compound

Structure

NPC57664 OpenBabel07101718182D 22 24 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 3.4641 1.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 2.5981 2.5000 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 0.5000 0.0000 C 0 0 2 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 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 9 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 1 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 13 19 1 6 0 0 0 14 17 1 1 0 0 0 14 20 1 0 0 0 0 15 16 1 6 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 4 1 1 0 0 0 17 9 1 1 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	310.324
LogP:	0.976
LogD:	0.297
LogS:	-3.514
# Rotatable Bonds:	4
TPSA:	79.29
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	5.254
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.077
MDCK Permeability:	1.8210090274806134e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.445
Human Intestinal Absorption (HIA):	0.165
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	33.8326301574707%
Volume Distribution (VD):	1.099
Pgp-substrate:	62.40914535522461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.642
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	1.985
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.448
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.839
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.933
Carcinogencity:	0.123
Eye Corrosion:	0.029
Eye Irritation:	0.076
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC57664

Natural Product ID:	NPC57664
*Common Name:**	Phomadecalin B
IUPAC Name:	2-[(1aS,2R,6R,7R,7aR,7bR)-2,6-dihydroxy-7,7a-dimethyl-2,6,7,7b-tetrahydronaphtho[1,2-b]oxiren-1a-yl]prop-2-enyl acetate
Synonyms:
Standard InCHIKey:	YSHGMEBFNCQBIY-GPJUBECRSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-9(8-21-11(3)18)17-14(20)7-12-5-6-13(19)10(2)16(12,4)15(17)22-17/h5-7,10,13-15,19-20H,1,8H2,2-4H3/t10-,13+,14+,15+,16+,17-/m0/s1
SMILES:	C=C(COC(=O)C)[C@]12[C@@H](C=C3C=C[C@H]([C@H](C)[C@@]3(C)[C@H]1O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448622
PubChem CID:	9995317
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33418	Phoma sp. NRRL 25697	Species	Didymellaceae	Eukaryota	Hypoxylon stromata	n.a.	n.a.	PMID[11908990]

☑ 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
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[522553]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[522553]

☑ 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 NPC57664 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	214
0.1-0.2	1234
0.2-0.3	4184
0.3-0.4	9694
0.4-0.5	14484
0.5-0.6	8377
0.6-0.7	3853
0.7-0.8	610
0.8-0.85	41
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC49783
0.8989	High Similarity	NPC281316
0.8696	High Similarity	NPC20946
0.8646	High Similarity	NPC205143
0.8571	High Similarity	NPC255143
0.8478	Intermediate Similarity	NPC131329
0.8478	Intermediate Similarity	NPC245004
0.8333	Intermediate Similarity	NPC469491
0.83	Intermediate Similarity	NPC11956
0.8298	Intermediate Similarity	NPC246028
0.8283	Intermediate Similarity	NPC38855
0.8265	Intermediate Similarity	NPC473244
0.8222	Intermediate Similarity	NPC474894
0.8218	Intermediate Similarity	NPC23584
0.8218	Intermediate Similarity	NPC473624
0.8211	Intermediate Similarity	NPC220216
0.8172	Intermediate Similarity	NPC61527
0.8163	Intermediate Similarity	NPC284194
0.8163	Intermediate Similarity	NPC471765
0.8163	Intermediate Similarity	NPC221801
0.8163	Intermediate Similarity	NPC211810
0.8155	Intermediate Similarity	NPC108682
0.8155	Intermediate Similarity	NPC469959
0.8155	Intermediate Similarity	NPC469957
0.8155	Intermediate Similarity	NPC472263
0.8144	Intermediate Similarity	NPC472360
0.8144	Intermediate Similarity	NPC472416
0.8125	Intermediate Similarity	NPC124374
0.8105	Intermediate Similarity	NPC261320
0.8105	Intermediate Similarity	NPC16265
0.81	Intermediate Similarity	NPC79303
0.8081	Intermediate Similarity	NPC182811
0.8065	Intermediate Similarity	NPC35933
0.8061	Intermediate Similarity	NPC240838
0.8058	Intermediate Similarity	NPC93026
0.8058	Intermediate Similarity	NPC29389
0.8058	Intermediate Similarity	NPC265502
0.8058	Intermediate Similarity	NPC469960
0.8043	Intermediate Similarity	NPC49208
0.8043	Intermediate Similarity	NPC231601
0.8043	Intermediate Similarity	NPC23748
0.8041	Intermediate Similarity	NPC99653
0.8021	Intermediate Similarity	NPC3952
0.8021	Intermediate Similarity	NPC191323
0.802	Intermediate Similarity	NPC475617
0.802	Intermediate Similarity	NPC472554
0.8019	Intermediate Similarity	NPC317107
0.8	Intermediate Similarity	NPC316974
0.8	Intermediate Similarity	NPC471537
0.8	Intermediate Similarity	NPC274458
0.8	Intermediate Similarity	NPC65700
0.8	Intermediate Similarity	NPC222303
0.798	Intermediate Similarity	NPC129569
0.7961	Intermediate Similarity	NPC473543
0.7957	Intermediate Similarity	NPC160517
0.7957	Intermediate Similarity	NPC78673
0.7957	Intermediate Similarity	NPC186155
0.7957	Intermediate Similarity	NPC83702
0.7944	Intermediate Similarity	NPC317687
0.7944	Intermediate Similarity	NPC470025
0.7944	Intermediate Similarity	NPC328074
0.7944	Intermediate Similarity	NPC317460
0.7944	Intermediate Similarity	NPC321272
0.7941	Intermediate Similarity	NPC472552
0.7941	Intermediate Similarity	NPC470571
0.7938	Intermediate Similarity	NPC477574
0.7935	Intermediate Similarity	NPC471408
0.7921	Intermediate Similarity	NPC79631
0.7921	Intermediate Similarity	NPC473510
0.7921	Intermediate Similarity	NPC271295
0.7905	Intermediate Similarity	NPC128795
0.7905	Intermediate Similarity	NPC217921
0.7905	Intermediate Similarity	NPC48548
0.7905	Intermediate Similarity	NPC50124
0.7905	Intermediate Similarity	NPC135015
0.7905	Intermediate Similarity	NPC311223
0.79	Intermediate Similarity	NPC261807
0.79	Intermediate Similarity	NPC120446
0.79	Intermediate Similarity	NPC96597
0.79	Intermediate Similarity	NPC98112
0.79	Intermediate Similarity	NPC239547
0.79	Intermediate Similarity	NPC91197
0.79	Intermediate Similarity	NPC125551
0.79	Intermediate Similarity	NPC476057
0.79	Intermediate Similarity	NPC309503
0.79	Intermediate Similarity	NPC155319
0.79	Intermediate Similarity	NPC210337
0.79	Intermediate Similarity	NPC347923
0.7895	Intermediate Similarity	NPC471779
0.7885	Intermediate Similarity	NPC82251
0.7879	Intermediate Similarity	NPC276110
0.787	Intermediate Similarity	NPC470027
0.7864	Intermediate Similarity	NPC134270
0.7864	Intermediate Similarity	NPC473523
0.7864	Intermediate Similarity	NPC474124
0.7857	Intermediate Similarity	NPC53555
0.785	Intermediate Similarity	NPC17791
0.785	Intermediate Similarity	NPC71680
0.7835	Intermediate Similarity	NPC48732
0.783	Intermediate Similarity	NPC40728
0.783	Intermediate Similarity	NPC472216
0.783	Intermediate Similarity	NPC5475
0.783	Intermediate Similarity	NPC284828
0.783	Intermediate Similarity	NPC173905
0.7822	Intermediate Similarity	NPC79449
0.7822	Intermediate Similarity	NPC247233
0.7822	Intermediate Similarity	NPC278673
0.7822	Intermediate Similarity	NPC474957
0.781	Intermediate Similarity	NPC88013
0.781	Intermediate Similarity	NPC67321
0.781	Intermediate Similarity	NPC187435
0.781	Intermediate Similarity	NPC125423
0.78	Intermediate Similarity	NPC473153
0.78	Intermediate Similarity	NPC288970
0.78	Intermediate Similarity	NPC88009
0.7798	Intermediate Similarity	NPC216665
0.7798	Intermediate Similarity	NPC305044
0.7798	Intermediate Similarity	NPC265290
0.7789	Intermediate Similarity	NPC311163
0.7788	Intermediate Similarity	NPC264867
0.7788	Intermediate Similarity	NPC201880
0.7788	Intermediate Similarity	NPC473207
0.7788	Intermediate Similarity	NPC81567
0.7788	Intermediate Similarity	NPC470321
0.7778	Intermediate Similarity	NPC105375
0.7778	Intermediate Similarity	NPC40049
0.7778	Intermediate Similarity	NPC182826
0.7767	Intermediate Similarity	NPC475038
0.7767	Intermediate Similarity	NPC476471
0.7767	Intermediate Similarity	NPC200672
0.7767	Intermediate Similarity	NPC471363
0.7767	Intermediate Similarity	NPC475344
0.7767	Intermediate Similarity	NPC214714
0.7767	Intermediate Similarity	NPC109195
0.7767	Intermediate Similarity	NPC472815
0.7767	Intermediate Similarity	NPC238397
0.7766	Intermediate Similarity	NPC102048
0.7757	Intermediate Similarity	NPC316708
0.7757	Intermediate Similarity	NPC472215
0.7757	Intermediate Similarity	NPC119550
0.7757	Intermediate Similarity	NPC177047
0.7757	Intermediate Similarity	NPC472214
0.7757	Intermediate Similarity	NPC15551
0.7748	Intermediate Similarity	NPC284707
0.7745	Intermediate Similarity	NPC188968
0.7745	Intermediate Similarity	NPC475053
0.7745	Intermediate Similarity	NPC230546
0.7736	Intermediate Similarity	NPC264819
0.7736	Intermediate Similarity	NPC38948
0.7736	Intermediate Similarity	NPC470024
0.7736	Intermediate Similarity	NPC181994
0.7736	Intermediate Similarity	NPC322903
0.7732	Intermediate Similarity	NPC128066
0.7732	Intermediate Similarity	NPC115607
0.7732	Intermediate Similarity	NPC82876
0.7714	Intermediate Similarity	NPC88349
0.7714	Intermediate Similarity	NPC477125
0.7714	Intermediate Similarity	NPC252296
0.7714	Intermediate Similarity	NPC470767
0.7714	Intermediate Similarity	NPC81630
0.7714	Intermediate Similarity	NPC471206
0.7714	Intermediate Similarity	NPC470763
0.7708	Intermediate Similarity	NPC166857
0.7706	Intermediate Similarity	NPC469454
0.7706	Intermediate Similarity	NPC101965
0.7706	Intermediate Similarity	NPC469496
0.7706	Intermediate Similarity	NPC469463
0.7706	Intermediate Similarity	NPC471204
0.7706	Intermediate Similarity	NPC101400
0.77	Intermediate Similarity	NPC37603
0.77	Intermediate Similarity	NPC471786
0.77	Intermediate Similarity	NPC8774
0.77	Intermediate Similarity	NPC476720
0.7692	Intermediate Similarity	NPC99266
0.7692	Intermediate Similarity	NPC7613
0.7692	Intermediate Similarity	NPC13823
0.7692	Intermediate Similarity	NPC7644
0.7692	Intermediate Similarity	NPC127933
0.7692	Intermediate Similarity	NPC475889
0.7692	Intermediate Similarity	NPC68119
0.7685	Intermediate Similarity	NPC470026
0.7685	Intermediate Similarity	NPC304180
0.7685	Intermediate Similarity	NPC255401
0.7685	Intermediate Similarity	NPC284162
0.7685	Intermediate Similarity	NPC179798
0.7685	Intermediate Similarity	NPC470076
0.7679	Intermediate Similarity	NPC278681
0.7677	Intermediate Similarity	NPC119379
0.7677	Intermediate Similarity	NPC205034
0.7677	Intermediate Similarity	NPC152778
0.7677	Intermediate Similarity	NPC310013
0.7677	Intermediate Similarity	NPC162615
0.767	Intermediate Similarity	NPC26557
0.767	Intermediate Similarity	NPC96784
0.767	Intermediate Similarity	NPC235920
0.767	Intermediate Similarity	NPC11974
0.767	Intermediate Similarity	NPC198992
0.767	Intermediate Similarity	NPC280991
0.7667	Intermediate Similarity	NPC301525
0.7664	Intermediate Similarity	NPC206618

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 NPC57664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1565
0.2-0.3	3611
0.3-0.4	2468
0.4-0.5	960
0.5-0.6	278
0.6-0.7	66
0.7-0.8	9
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
0.802	Intermediate Similarity	NPD5344	Discontinued
0.7921	Intermediate Similarity	NPD6648	Approved
0.7835	Intermediate Similarity	NPD7838	Discovery
0.7677	Intermediate Similarity	NPD5779	Approved
0.7677	Intermediate Similarity	NPD5778	Approved
0.7476	Intermediate Similarity	NPD4225	Approved
0.7347	Intermediate Similarity	NPD7524	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.7339	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD46	Approved
0.73	Intermediate Similarity	NPD6698	Approved
0.7228	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7216	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8264	Approved
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6695	Phase 3
0.7094	Intermediate Similarity	NPD7503	Approved
0.7075	Intermediate Similarity	NPD7639	Approved
0.7075	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD7983	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6101	Approved
0.6981	Remote Similarity	NPD7638	Approved
0.6964	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8517	Approved
0.6949	Remote Similarity	NPD8513	Phase 3
0.6949	Remote Similarity	NPD8515	Approved
0.6949	Remote Similarity	NPD8516	Approved
0.6869	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7327	Approved
0.6838	Remote Similarity	NPD7328	Approved
0.6832	Remote Similarity	NPD7750	Discontinued
0.6814	Remote Similarity	NPD6371	Approved
0.6807	Remote Similarity	NPD8033	Approved
0.6804	Remote Similarity	NPD7332	Phase 2
0.6804	Remote Similarity	NPD7514	Phase 3
0.6804	Remote Similarity	NPD6931	Approved
0.6804	Remote Similarity	NPD6930	Phase 2
0.6786	Remote Similarity	NPD6686	Approved
0.678	Remote Similarity	NPD7516	Approved
0.6735	Remote Similarity	NPD6902	Approved
0.6723	Remote Similarity	NPD8377	Approved
0.6723	Remote Similarity	NPD8294	Approved
0.6701	Remote Similarity	NPD6929	Approved
0.6696	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7145	Approved
0.6571	Remote Similarity	NPD7087	Discontinued
0.6562	Remote Similarity	NPD6933	Approved
0.6545	Remote Similarity	NPD4159	Approved
0.6538	Remote Similarity	NPD6051	Approved
0.6509	Remote Similarity	NPD6399	Phase 3
0.6505	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4632	Approved
0.6495	Remote Similarity	NPD6932	Approved
0.6495	Remote Similarity	NPD6925	Approved
0.6495	Remote Similarity	NPD5776	Phase 2
0.6486	Remote Similarity	NPD7632	Discontinued
0.6476	Remote Similarity	NPD3168	Discontinued
0.6471	Remote Similarity	NPD6893	Approved
0.6465	Remote Similarity	NPD4819	Approved
0.6465	Remote Similarity	NPD4820	Approved
0.6465	Remote Similarity	NPD4822	Approved
0.6465	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4821	Approved
0.646	Remote Similarity	NPD6640	Phase 3
0.6458	Remote Similarity	NPD8039	Approved
0.6452	Remote Similarity	NPD7507	Approved
0.6446	Remote Similarity	NPD6319	Approved
0.6444	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8297	Approved
0.641	Remote Similarity	NPD6053	Discontinued
0.6408	Remote Similarity	NPD4249	Approved
0.6404	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD6898	Phase 1
0.6374	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7645	Phase 2
0.6356	Remote Similarity	NPD8133	Approved
0.6354	Remote Similarity	NPD6926	Approved
0.6354	Remote Similarity	NPD6924	Approved
0.6348	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD4251	Approved
0.6346	Remote Similarity	NPD4250	Approved
0.633	Remote Similarity	NPD7839	Suspended
0.633	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8273	Phase 1
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6311	Remote Similarity	NPD1696	Phase 3
0.63	Remote Similarity	NPD7509	Discontinued
0.63	Remote Similarity	NPD7525	Registered
0.63	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7319	Approved
0.6296	Remote Similarity	NPD7748	Approved
0.6293	Remote Similarity	NPD6014	Approved
0.6293	Remote Similarity	NPD6013	Approved
0.6293	Remote Similarity	NPD6012	Approved
0.6275	Remote Similarity	NPD7154	Phase 3
0.6273	Remote Similarity	NPD7902	Approved
0.6263	Remote Similarity	NPD4271	Approved
0.6263	Remote Similarity	NPD4268	Approved
0.6262	Remote Similarity	NPD5284	Approved
0.6262	Remote Similarity	NPD5281	Approved
0.6262	Remote Similarity	NPD7515	Phase 2
0.6261	Remote Similarity	NPD6412	Phase 2
0.6261	Remote Similarity	NPD5701	Approved
0.6261	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4732	Discontinued
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD5695	Phase 3
0.6239	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6224	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD368	Approved
0.6207	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD6011	Approved
0.6202	Remote Similarity	NPD7260	Phase 2
0.62	Remote Similarity	NPD6683	Phase 2
0.6198	Remote Similarity	NPD4198	Discontinued
0.6198	Remote Similarity	NPD6009	Approved
0.6195	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5211	Phase 2
0.6186	Remote Similarity	NPD6650	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6186	Remote Similarity	NPD6649	Approved
0.6186	Remote Similarity	NPD6869	Approved
0.6176	Remote Similarity	NPD5209	Approved
0.6176	Remote Similarity	NPD3667	Approved
0.6176	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5785	Approved
0.616	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6372	Approved
0.6146	Remote Similarity	NPD7150	Approved
0.6146	Remote Similarity	NPD7152	Approved
0.6146	Remote Similarity	NPD7151	Approved
0.6134	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD5983	Phase 2
0.6126	Remote Similarity	NPD6084	Phase 2
0.6126	Remote Similarity	NPD6083	Phase 2
0.6122	Remote Similarity	NPD6942	Approved
0.6122	Remote Similarity	NPD7339	Approved
0.6117	Remote Similarity	NPD5362	Discontinued
0.6111	Remote Similarity	NPD7492	Approved
0.6102	Remote Similarity	NPD4634	Approved
0.61	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5141	Approved
0.6075	Remote Similarity	NPD1695	Approved
0.6066	Remote Similarity	NPD7505	Discontinued
0.6066	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6616	Approved
0.6058	Remote Similarity	NPD4786	Approved
0.6048	Remote Similarity	NPD6054	Approved
0.6044	Remote Similarity	NPD4193	Approved
0.6044	Remote Similarity	NPD4192	Approved
0.6044	Remote Similarity	NPD4194	Approved
0.6044	Remote Similarity	NPD4191	Approved
0.6042	Remote Similarity	NPD7143	Approved
0.6042	Remote Similarity	NPD7144	Approved
0.6032	Remote Similarity	NPD7829	Approved
0.6032	Remote Similarity	NPD8328	Phase 3
0.6032	Remote Similarity	NPD7830	Approved
0.6019	Remote Similarity	NPD7136	Phase 2
0.6018	Remote Similarity	NPD5285	Approved
0.6018	Remote Similarity	NPD5286	Approved
0.6018	Remote Similarity	NPD4696	Approved
0.6016	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6921	Approved
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.5984	Remote Similarity	NPD2629	Approved
0.5982	Remote Similarity	NPD4755	Approved
0.598	Remote Similarity	NPD4748	Discontinued
0.5969	Remote Similarity	NPD7736	Approved
0.5963	Remote Similarity	NPD5694	Approved
0.5962	Remote Similarity	NPD5331	Approved
0.5962	Remote Similarity	NPD5332	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