NPASS Compound

Structure

NPC58271 OpenBabel07101719512D 23 25 0 0 1 0 0 0 0 0999 V2000 2.8431 2.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9789 0.3519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4597 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4283 0.3762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9143 1.8903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 -1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 0.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8327 -0.4808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8327 2.4038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 1.4423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 19 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 2 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 18 4 1 6 0 0 0 19 20 1 1 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	3.477
LogD:	2.862
LogS:	-5.318
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	4.808
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.813
MDCK Permeability:	2.1423440557555296e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.328
Plasma Protein Binding (PPB):	91.79085540771484%
Volume Distribution (VD):	0.835
Pgp-substrate:	5.412637233734131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.51
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	2.562
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.09
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.222
Carcinogencity:	0.956
Eye Corrosion:	0.028
Eye Irritation:	0.082
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: NPC58271

Natural Product ID:	NPC58271
*Common Name:**	(4As,4Bs,7R)-7-Ethenyl-4B,10-Dihydroxy-1,1,4A,7-Tetramethyl-3,4,5,6-Tetrahydro-2H-Phenanthren-9-One
IUPAC Name:	(4aS,4bS,7R)-7-ethenyl-4b,10-dihydroxy-1,1,4a,7-tetramethyl-3,4,5,6-tetrahydro-2H-phenanthren-9-one
Synonyms:
Standard InCHIKey:	UUOWQGQDPSMWOB-SLFFLAALSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-6-18(4)10-11-20(23)13(12-18)14(21)15(22)16-17(2,3)8-7-9-19(16,20)5/h6,12,22-23H,1,7-11H2,2-5H3/t18-,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@]2(C(=C1)C(=O)C(=C1C(C)(C)CCC[C@]21C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017493
PubChem CID:	57404389
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO33396	Epicoccum sp. HS-1	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418279]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	20.74	ug.mL-1	PMID[533240]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.47	ug.mL-1	PMID[533240]

☑ 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 NPC58271 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	175
0.1-0.2	1242
0.2-0.3	5115
0.3-0.4	11848
0.4-0.5	14076
0.5-0.6	6941
0.6-0.7	2840
0.7-0.8	421
0.8-0.85	34
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8817	High Similarity	NPC470184
0.8632	High Similarity	NPC230918
0.8539	High Similarity	NPC474918
0.8427	Intermediate Similarity	NPC471791
0.8427	Intermediate Similarity	NPC471793
0.8353	Intermediate Similarity	NPC108955
0.8315	Intermediate Similarity	NPC220930
0.8315	Intermediate Similarity	NPC272039
0.8256	Intermediate Similarity	NPC55869
0.8256	Intermediate Similarity	NPC225515
0.8202	Intermediate Similarity	NPC472974
0.82	Intermediate Similarity	NPC20192
0.8171	Intermediate Similarity	NPC247586
0.8095	Intermediate Similarity	NPC92080
0.809	Intermediate Similarity	NPC255174
0.8065	Intermediate Similarity	NPC131840
0.8022	Intermediate Similarity	NPC307298
0.8022	Intermediate Similarity	NPC72397
0.8022	Intermediate Similarity	NPC53454
0.8	Intermediate Similarity	NPC472488
0.7978	Intermediate Similarity	NPC40687
0.7957	Intermediate Similarity	NPC73457
0.7957	Intermediate Similarity	NPC26865
0.7955	Intermediate Similarity	NPC92226
0.7955	Intermediate Similarity	NPC103486
0.7935	Intermediate Similarity	NPC472676
0.7935	Intermediate Similarity	NPC472688
0.7931	Intermediate Similarity	NPC469637
0.7931	Intermediate Similarity	NPC476809
0.7912	Intermediate Similarity	NPC471792
0.7907	Intermediate Similarity	NPC275494
0.7907	Intermediate Similarity	NPC207772
0.7907	Intermediate Similarity	NPC476808
0.7907	Intermediate Similarity	NPC30321
0.7907	Intermediate Similarity	NPC471409
0.7895	Intermediate Similarity	NPC147232
0.7889	Intermediate Similarity	NPC70685
0.7889	Intermediate Similarity	NPC132228
0.7889	Intermediate Similarity	NPC263997
0.7889	Intermediate Similarity	NPC8518
0.7889	Intermediate Similarity	NPC33663
0.7882	Intermediate Similarity	NPC1254
0.7865	Intermediate Similarity	NPC105803
0.7849	Intermediate Similarity	NPC113393
0.7843	Intermediate Similarity	NPC220705
0.7841	Intermediate Similarity	NPC226068
0.7826	Intermediate Similarity	NPC48107
0.7816	Intermediate Similarity	NPC27817
0.7816	Intermediate Similarity	NPC170394
0.781	Intermediate Similarity	NPC261330
0.7802	Intermediate Similarity	NPC470955
0.7802	Intermediate Similarity	NPC472479
0.7802	Intermediate Similarity	NPC194417
0.7791	Intermediate Similarity	NPC34110
0.7791	Intermediate Similarity	NPC257666
0.7791	Intermediate Similarity	NPC266193
0.7778	Intermediate Similarity	NPC476412
0.7742	Intermediate Similarity	NPC472489
0.7742	Intermediate Similarity	NPC65615
0.7742	Intermediate Similarity	NPC68148
0.7742	Intermediate Similarity	NPC472973
0.7732	Intermediate Similarity	NPC273269
0.7727	Intermediate Similarity	NPC148685
0.7727	Intermediate Similarity	NPC104120
0.7727	Intermediate Similarity	NPC157895
0.7723	Intermediate Similarity	NPC32006
0.7723	Intermediate Similarity	NPC85529
0.7701	Intermediate Similarity	NPC189485
0.77	Intermediate Similarity	NPC131366
0.7692	Intermediate Similarity	NPC6185
0.7692	Intermediate Similarity	NPC79573
0.7692	Intermediate Similarity	NPC476426
0.7692	Intermediate Similarity	NPC469993
0.7692	Intermediate Similarity	NPC241512
0.7692	Intermediate Similarity	NPC474680
0.7684	Intermediate Similarity	NPC271652
0.7674	Intermediate Similarity	NPC110725
0.7674	Intermediate Similarity	NPC472305
0.7667	Intermediate Similarity	NPC169941
0.7667	Intermediate Similarity	NPC258985
0.7667	Intermediate Similarity	NPC53733
0.7667	Intermediate Similarity	NPC251475
0.7667	Intermediate Similarity	NPC49019
0.766	Intermediate Similarity	NPC474209
0.766	Intermediate Similarity	NPC475823
0.766	Intermediate Similarity	NPC230332
0.7653	Intermediate Similarity	NPC316598
0.764	Intermediate Similarity	NPC116797
0.764	Intermediate Similarity	NPC473217
0.764	Intermediate Similarity	NPC474085
0.7629	Intermediate Similarity	NPC272411
0.7614	Intermediate Similarity	NPC308038
0.7609	Intermediate Similarity	NPC472985
0.7609	Intermediate Similarity	NPC472986
0.7604	Intermediate Similarity	NPC23170
0.7604	Intermediate Similarity	NPC472977
0.7604	Intermediate Similarity	NPC160413
0.7604	Intermediate Similarity	NPC472976
0.7604	Intermediate Similarity	NPC474882
0.7586	Intermediate Similarity	NPC97377
0.7582	Intermediate Similarity	NPC251170
0.7579	Intermediate Similarity	NPC99380
0.7579	Intermediate Similarity	NPC172101
0.7579	Intermediate Similarity	NPC472978
0.7576	Intermediate Similarity	NPC46761
0.7558	Intermediate Similarity	NPC175079
0.7553	Intermediate Similarity	NPC118011
0.7553	Intermediate Similarity	NPC36668
0.7553	Intermediate Similarity	NPC472983
0.7553	Intermediate Similarity	NPC472475
0.7553	Intermediate Similarity	NPC472477
0.7528	Intermediate Similarity	NPC233352
0.7528	Intermediate Similarity	NPC138492
0.7528	Intermediate Similarity	NPC824
0.7528	Intermediate Similarity	NPC472301
0.7527	Intermediate Similarity	NPC476409
0.7526	Intermediate Similarity	NPC259286
0.7526	Intermediate Similarity	NPC280725
0.7526	Intermediate Similarity	NPC474602
0.7526	Intermediate Similarity	NPC476245
0.7525	Intermediate Similarity	NPC111323
0.7525	Intermediate Similarity	NPC320154
0.75	Intermediate Similarity	NPC62336
0.75	Intermediate Similarity	NPC32037
0.75	Intermediate Similarity	NPC248624
0.75	Intermediate Similarity	NPC163372
0.75	Intermediate Similarity	NPC300026
0.75	Intermediate Similarity	NPC302537
0.75	Intermediate Similarity	NPC115862
0.75	Intermediate Similarity	NPC475994
0.75	Intermediate Similarity	NPC211230
0.7476	Intermediate Similarity	NPC472925
0.7474	Intermediate Similarity	NPC472476
0.7474	Intermediate Similarity	NPC134321
0.7474	Intermediate Similarity	NPC38952
0.7471	Intermediate Similarity	NPC7629
0.7471	Intermediate Similarity	NPC186554
0.7471	Intermediate Similarity	NPC76966
0.7471	Intermediate Similarity	NPC470525
0.7471	Intermediate Similarity	NPC263582
0.7471	Intermediate Similarity	NPC151622
0.7449	Intermediate Similarity	NPC117133
0.7449	Intermediate Similarity	NPC249954
0.7444	Intermediate Similarity	NPC472684
0.7444	Intermediate Similarity	NPC14151
0.7444	Intermediate Similarity	NPC44963
0.7426	Intermediate Similarity	NPC119601
0.7426	Intermediate Similarity	NPC308726
0.7423	Intermediate Similarity	NPC212812
0.7423	Intermediate Similarity	NPC474328
0.7423	Intermediate Similarity	NPC78159
0.7419	Intermediate Similarity	NPC82979
0.7419	Intermediate Similarity	NPC94666
0.7416	Intermediate Similarity	NPC192329
0.7416	Intermediate Similarity	NPC281138
0.7416	Intermediate Similarity	NPC19900
0.7412	Intermediate Similarity	NPC84790
0.7404	Intermediate Similarity	NPC168883
0.7396	Intermediate Similarity	NPC475806
0.7396	Intermediate Similarity	NPC204341
0.7396	Intermediate Similarity	NPC472975
0.7391	Intermediate Similarity	NPC144258
0.7386	Intermediate Similarity	NPC149550
0.7386	Intermediate Similarity	NPC165711
0.7386	Intermediate Similarity	NPC85105
0.7381	Intermediate Similarity	NPC136473
0.7379	Intermediate Similarity	NPC166607
0.7374	Intermediate Similarity	NPC170131
0.7374	Intermediate Similarity	NPC471916
0.7368	Intermediate Similarity	NPC112454
0.7368	Intermediate Similarity	NPC262043
0.7363	Intermediate Similarity	NPC48362
0.7363	Intermediate Similarity	NPC158411
0.7363	Intermediate Similarity	NPC38796
0.7363	Intermediate Similarity	NPC238991
0.7363	Intermediate Similarity	NPC302661
0.7363	Intermediate Similarity	NPC93590
0.7353	Intermediate Similarity	NPC249187
0.7353	Intermediate Similarity	NPC311612
0.7353	Intermediate Similarity	NPC247957
0.7347	Intermediate Similarity	NPC777
0.7347	Intermediate Similarity	NPC272617
0.734	Intermediate Similarity	NPC231599
0.734	Intermediate Similarity	NPC298904
0.7339	Intermediate Similarity	NPC477116
0.7339	Intermediate Similarity	NPC27999
0.7333	Intermediate Similarity	NPC18955
0.7333	Intermediate Similarity	NPC2482
0.7333	Intermediate Similarity	NPC45495
0.7333	Intermediate Similarity	NPC87335
0.7333	Intermediate Similarity	NPC172013
0.7333	Intermediate Similarity	NPC26139
0.7326	Intermediate Similarity	NPC153660
0.732	Intermediate Similarity	NPC69454
0.732	Intermediate Similarity	NPC474807
0.732	Intermediate Similarity	NPC474736
0.732	Intermediate Similarity	NPC476416
0.732	Intermediate Similarity	NPC134826
0.732	Intermediate Similarity	NPC109305
0.7312	Intermediate Similarity	NPC474853

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 NPC58271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1640
0.2-0.3	3804
0.3-0.4	2411
0.4-0.5	716
0.5-0.6	232
0.6-0.7	150
0.7-0.8	12
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
0.814	Intermediate Similarity	NPD4695	Discontinued
0.7802	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD5690	Phase 2
0.7609	Intermediate Similarity	NPD4519	Discontinued
0.7609	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD3617	Approved
0.7426	Intermediate Similarity	NPD5211	Phase 2
0.7419	Intermediate Similarity	NPD5280	Approved
0.7419	Intermediate Similarity	NPD4694	Approved
0.7391	Intermediate Similarity	NPD4197	Approved
0.7368	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5329	Approved
0.7282	Intermediate Similarity	NPD5141	Approved
0.7234	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD4696	Approved
0.7228	Intermediate Similarity	NPD5286	Approved
0.7228	Intermediate Similarity	NPD5285	Approved
0.7174	Intermediate Similarity	NPD4221	Approved
0.7174	Intermediate Similarity	NPD4223	Phase 3
0.7157	Intermediate Similarity	NPD5223	Approved
0.7128	Intermediate Similarity	NPD1696	Phase 3
0.71	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5222	Approved
0.71	Intermediate Similarity	NPD5221	Approved
0.7087	Intermediate Similarity	NPD4633	Approved
0.7087	Intermediate Similarity	NPD5226	Approved
0.7087	Intermediate Similarity	NPD5224	Approved
0.7087	Intermediate Similarity	NPD5225	Approved
0.7053	Intermediate Similarity	NPD3618	Phase 1
0.7041	Intermediate Similarity	NPD5281	Approved
0.7041	Intermediate Similarity	NPD6079	Approved
0.7041	Intermediate Similarity	NPD5284	Approved
0.703	Intermediate Similarity	NPD4755	Approved
0.703	Intermediate Similarity	NPD5173	Approved
0.7019	Intermediate Similarity	NPD5174	Approved
0.7019	Intermediate Similarity	NPD5175	Approved
0.701	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD5210	Approved
0.7	Intermediate Similarity	NPD4629	Approved
0.6979	Remote Similarity	NPD3573	Approved
0.697	Remote Similarity	NPD4202	Approved
0.697	Remote Similarity	NPD5133	Approved
0.6944	Remote Similarity	NPD4634	Approved
0.6907	Remote Similarity	NPD4518	Approved
0.6893	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD5205	Approved
0.6875	Remote Similarity	NPD4693	Phase 3
0.6875	Remote Similarity	NPD4138	Approved
0.6875	Remote Similarity	NPD4689	Approved
0.6875	Remote Similarity	NPD4688	Approved
0.6875	Remote Similarity	NPD4690	Approved
0.6867	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4195	Approved
0.6842	Remote Similarity	NPD3666	Approved
0.6842	Remote Similarity	NPD3665	Phase 1
0.6842	Remote Similarity	NPD3133	Approved
0.6837	Remote Similarity	NPD5328	Approved
0.6832	Remote Similarity	NPD5695	Phase 3
0.6822	Remote Similarity	NPD5697	Approved
0.6809	Remote Similarity	NPD3667	Approved
0.6774	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4096	Approved
0.6765	Remote Similarity	NPD4697	Phase 3
0.6759	Remote Similarity	NPD6881	Approved
0.6759	Remote Similarity	NPD6899	Approved
0.6759	Remote Similarity	NPD4730	Approved
0.6759	Remote Similarity	NPD4729	Approved
0.6759	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD5282	Discontinued
0.6726	Remote Similarity	NPD7115	Discovery
0.6702	Remote Similarity	NPD4139	Approved
0.6702	Remote Similarity	NPD4692	Approved
0.67	Remote Similarity	NPD7515	Phase 2
0.67	Remote Similarity	NPD5694	Approved
0.6698	Remote Similarity	NPD4754	Approved
0.6697	Remote Similarity	NPD6014	Approved
0.6697	Remote Similarity	NPD6013	Approved
0.6697	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5249	Phase 3
0.6628	Remote Similarity	NPD7331	Phase 2
0.6606	Remote Similarity	NPD5128	Approved
0.6604	Remote Similarity	NPD5091	Approved
0.66	Remote Similarity	NPD5692	Phase 3
0.6598	Remote Similarity	NPD1694	Approved
0.6577	Remote Similarity	NPD8130	Phase 1
0.6577	Remote Similarity	NPD5216	Approved
0.6577	Remote Similarity	NPD5127	Approved
0.6577	Remote Similarity	NPD5215	Approved
0.6577	Remote Similarity	NPD6847	Approved
0.6577	Remote Similarity	NPD5217	Approved
0.6577	Remote Similarity	NPD6650	Approved
0.6577	Remote Similarity	NPD6649	Approved
0.6577	Remote Similarity	NPD6869	Approved
0.6577	Remote Similarity	NPD6617	Approved
0.6574	Remote Similarity	NPD5739	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD4767	Approved
0.6574	Remote Similarity	NPD4768	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6569	Remote Similarity	NPD7748	Approved
0.6538	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD7902	Approved
0.6535	Remote Similarity	NPD5693	Phase 1
0.6535	Remote Similarity	NPD6050	Approved
0.6535	Remote Similarity	NPD6411	Approved
0.6518	Remote Similarity	NPD6882	Approved
0.6518	Remote Similarity	NPD8297	Approved
0.6517	Remote Similarity	NPD4691	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.6512	Remote Similarity	NPD7341	Phase 2
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6904	Approved
0.6484	Remote Similarity	NPD4687	Approved
0.6484	Remote Similarity	NPD4058	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6476	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.646	Remote Similarity	NPD4632	Approved
0.6458	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5168	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6452	Remote Similarity	NPD4756	Discovery
0.6444	Remote Similarity	NPD5276	Approved
0.6442	Remote Similarity	NPD7614	Phase 1
0.6436	Remote Similarity	NPD5207	Approved
0.6415	Remote Similarity	NPD6404	Discontinued
0.641	Remote Similarity	NPD6319	Approved
0.641	Remote Similarity	NPD6054	Approved
0.6404	Remote Similarity	NPD4137	Phase 3
0.6404	Remote Similarity	NPD5167	Approved
0.64	Remote Similarity	NPD5737	Approved
0.64	Remote Similarity	NPD6672	Approved
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD6372	Approved
0.6392	Remote Similarity	NPD4788	Approved
0.6364	Remote Similarity	NPD6098	Approved
0.6356	Remote Similarity	NPD6016	Approved
0.6356	Remote Similarity	NPD6015	Approved
0.6346	Remote Similarity	NPD5654	Approved
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4747	Approved
0.6327	Remote Similarity	NPD3668	Phase 3
0.6311	Remote Similarity	NPD6399	Phase 3
0.6304	Remote Similarity	NPD5733	Approved
0.6303	Remote Similarity	NPD6370	Approved
0.6303	Remote Similarity	NPD5988	Approved
0.6293	Remote Similarity	NPD6317	Approved
0.6293	Remote Similarity	NPD6009	Approved
0.6289	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5785	Approved
0.6263	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6001	Approved
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6313	Approved
0.6239	Remote Similarity	NPD6335	Approved
0.6239	Remote Similarity	NPD6314	Approved
0.6238	Remote Similarity	NPD5208	Approved
0.6237	Remote Similarity	NPD8264	Approved
0.6226	Remote Similarity	NPD5959	Approved
0.6207	Remote Similarity	NPD6274	Approved
0.62	Remote Similarity	NPD7146	Approved
0.62	Remote Similarity	NPD6409	Approved
0.62	Remote Similarity	NPD7334	Approved
0.62	Remote Similarity	NPD7521	Approved
0.62	Remote Similarity	NPD6684	Approved
0.62	Remote Similarity	NPD5330	Approved
0.6198	Remote Similarity	NPD7492	Approved
0.619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7100	Approved
0.6186	Remote Similarity	NPD4522	Approved
0.6186	Remote Similarity	NPD7101	Approved
0.6161	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6616	Approved
0.6134	Remote Similarity	NPD6059	Approved
0.6129	Remote Similarity	NPD4785	Approved
0.6129	Remote Similarity	NPD4784	Approved
0.6111	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD7639	Approved
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7078	Approved
0.6083	Remote Similarity	NPD6291	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