NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.17
Volume:	271.981
LogP:	1.582
LogD:	0.609
LogS:	-1.453
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	4.564
Fsp3:	0.8
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:	-4.976
MDCK Permeability:	1.0960303370666225e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.656
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.612
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.795
Plasma Protein Binding (PPB):	57.809818267822266%
Volume Distribution (VD):	0.735
Pgp-substrate:	33.52914810180664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.241
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	6.185
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.76
Carcinogencity:	0.074
Eye Corrosion:	0.928
Eye Irritation:	0.903
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC64600

Natural Product ID:	NPC64600
*Common Name:**	Kandenol A
IUPAC Name:	(4aR,6R,7R,8aS)-7-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-1,4a,5,6,7,8-hexahydronaphthalen-2-one
Synonyms:	Kandenol A
Standard InCHIKey:	MEPRCLDIBSGQBP-KYEXWDHISA-N
Standard InCHI:	InChI=1S/C15H24O3/c1-9-5-10(16)7-15(4)8-13(17)12(6-11(9)15)14(2,3)18/h5,11-13,17-18H,6-8H2,1-4H3/t11-,12+,13+,15+/m0/s1
SMILES:	O=C1C=C(C)[C@H]2[C@@](C1)(C)C[C@H]([C@@H](C2)C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208380
PubChem CID:	71463282
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO33639	Streptomyces sp. HKI0595	Species	Streptomycetaceae	Bacteria	Isolated from the stems of Mangrove Tree Kandelia candel	Xiamen, Fujian Province, China	2002-JUN	PMID[23234344]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	100.0	ug.mL-1	PMID[531557]
NPT3473	Organism	Mycobacterium vaccae	Mycobacterium vaccae	MIC	=	12.5	ug.mL-1	PMID[531557]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[531557]

☑ 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 NPC64600 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	176
0.1-0.2	1214
0.2-0.3	5078
0.3-0.4	11604
0.4-0.5	11616
0.5-0.6	6471
0.6-0.7	4743
0.7-0.8	1634
0.8-0.85	131
0.85-0.9	26
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC197659
0.9167	High Similarity	NPC134321
0.9167	High Similarity	NPC128672
0.8929	High Similarity	NPC328539
0.8902	High Similarity	NPC470812
0.8875	High Similarity	NPC172013
0.8837	High Similarity	NPC472978
0.8824	High Similarity	NPC86319
0.8824	High Similarity	NPC472973
0.8824	High Similarity	NPC275740
0.8765	High Similarity	NPC119229
0.875	High Similarity	NPC308038
0.875	High Similarity	NPC473170
0.875	High Similarity	NPC316215
0.8734	High Similarity	NPC266193
0.8734	High Similarity	NPC257666
0.8706	High Similarity	NPC143767
0.8706	High Similarity	NPC131470
0.8706	High Similarity	NPC158778
0.869	High Similarity	NPC179591
0.8675	High Similarity	NPC40687
0.8659	High Similarity	NPC93590
0.8636	High Similarity	NPC196227
0.8636	High Similarity	NPC103527
0.8625	High Similarity	NPC178852
0.8625	High Similarity	NPC62336
0.8625	High Similarity	NPC80088
0.8625	High Similarity	NPC253561
0.8621	High Similarity	NPC168027
0.8621	High Similarity	NPC472975
0.8621	High Similarity	NPC185936
0.8621	High Similarity	NPC116726
0.8608	High Similarity	NPC76966
0.8608	High Similarity	NPC263582
0.8608	High Similarity	NPC186554
0.8571	High Similarity	NPC470574
0.8556	High Similarity	NPC18509
0.8554	High Similarity	NPC105173
0.8539	High Similarity	NPC259286
0.8537	High Similarity	NPC473420
0.8523	High Similarity	NPC69454
0.8519	High Similarity	NPC281138
0.8506	High Similarity	NPC230332
0.8506	High Similarity	NPC183283
0.8488	Intermediate Similarity	NPC310752
0.8488	Intermediate Similarity	NPC292491
0.8488	Intermediate Similarity	NPC474925
0.8488	Intermediate Similarity	NPC471722
0.8488	Intermediate Similarity	NPC472802
0.8481	Intermediate Similarity	NPC114236
0.8471	Intermediate Similarity	NPC158393
0.8471	Intermediate Similarity	NPC94666
0.8471	Intermediate Similarity	NPC72133
0.8471	Intermediate Similarity	NPC213412
0.8471	Intermediate Similarity	NPC472974
0.8471	Intermediate Similarity	NPC472985
0.8471	Intermediate Similarity	NPC472986
0.8452	Intermediate Similarity	NPC251170
0.8444	Intermediate Similarity	NPC249954
0.8434	Intermediate Similarity	NPC48362
0.8434	Intermediate Similarity	NPC70479
0.8427	Intermediate Similarity	NPC472977
0.8427	Intermediate Similarity	NPC472976
0.8427	Intermediate Similarity	NPC471207
0.8415	Intermediate Similarity	NPC476809
0.8415	Intermediate Similarity	NPC104120
0.8415	Intermediate Similarity	NPC157895
0.8415	Intermediate Similarity	NPC148685
0.8415	Intermediate Similarity	NPC2482
0.8409	Intermediate Similarity	NPC99380
0.8409	Intermediate Similarity	NPC63748
0.8395	Intermediate Similarity	NPC207772
0.8391	Intermediate Similarity	NPC69627
0.8391	Intermediate Similarity	NPC1015
0.8391	Intermediate Similarity	NPC119416
0.8391	Intermediate Similarity	NPC472983
0.8391	Intermediate Similarity	NPC31985
0.8375	Intermediate Similarity	NPC470525
0.8375	Intermediate Similarity	NPC472305
0.8375	Intermediate Similarity	NPC250621
0.8372	Intermediate Similarity	NPC298904
0.8372	Intermediate Similarity	NPC472324
0.8372	Intermediate Similarity	NPC141292
0.8372	Intermediate Similarity	NPC475740
0.837	Intermediate Similarity	NPC144956
0.8354	Intermediate Similarity	NPC470299
0.8353	Intermediate Similarity	NPC133954
0.8333	Intermediate Similarity	NPC251475
0.8333	Intermediate Similarity	NPC110150
0.8333	Intermediate Similarity	NPC169941
0.8333	Intermediate Similarity	NPC66764
0.8333	Intermediate Similarity	NPC278648
0.8333	Intermediate Similarity	NPC139570
0.8333	Intermediate Similarity	NPC476082
0.8333	Intermediate Similarity	NPC476245
0.8315	Intermediate Similarity	NPC472930
0.8315	Intermediate Similarity	NPC477436
0.8315	Intermediate Similarity	NPC477435
0.8313	Intermediate Similarity	NPC121984
0.8313	Intermediate Similarity	NPC226068
0.8313	Intermediate Similarity	NPC473217
0.8295	Intermediate Similarity	NPC85173
0.8295	Intermediate Similarity	NPC473099
0.8295	Intermediate Similarity	NPC191684
0.8276	Intermediate Similarity	NPC473229
0.8276	Intermediate Similarity	NPC206060
0.8272	Intermediate Similarity	NPC325946
0.8272	Intermediate Similarity	NPC74995
0.8272	Intermediate Similarity	NPC34110
0.8256	Intermediate Similarity	NPC327115
0.8256	Intermediate Similarity	NPC31564
0.8256	Intermediate Similarity	NPC145879
0.8256	Intermediate Similarity	NPC475862
0.8256	Intermediate Similarity	NPC474732
0.8256	Intermediate Similarity	NPC474733
0.8256	Intermediate Similarity	NPC474778
0.8256	Intermediate Similarity	NPC73038
0.8256	Intermediate Similarity	NPC74363
0.8242	Intermediate Similarity	NPC469545
0.8242	Intermediate Similarity	NPC5532
0.8242	Intermediate Similarity	NPC192428
0.8242	Intermediate Similarity	NPC61369
0.8235	Intermediate Similarity	NPC329043
0.8235	Intermediate Similarity	NPC214043
0.8235	Intermediate Similarity	NPC58841
0.8235	Intermediate Similarity	NPC473246
0.8235	Intermediate Similarity	NPC321187
0.8235	Intermediate Similarity	NPC161423
0.8235	Intermediate Similarity	NPC227064
0.8235	Intermediate Similarity	NPC85774
0.8235	Intermediate Similarity	NPC476412
0.8222	Intermediate Similarity	NPC473172
0.8222	Intermediate Similarity	NPC166906
0.8214	Intermediate Similarity	NPC470813
0.8214	Intermediate Similarity	NPC151519
0.8202	Intermediate Similarity	NPC158030
0.8202	Intermediate Similarity	NPC65120
0.8202	Intermediate Similarity	NPC4036
0.8202	Intermediate Similarity	NPC131872
0.8202	Intermediate Similarity	NPC233455
0.8202	Intermediate Similarity	NPC475806
0.8202	Intermediate Similarity	NPC145067
0.8202	Intermediate Similarity	NPC272746
0.8193	Intermediate Similarity	NPC469637
0.8193	Intermediate Similarity	NPC472301
0.8182	Intermediate Similarity	NPC309603
0.8182	Intermediate Similarity	NPC473100
0.8182	Intermediate Similarity	NPC473999
0.8182	Intermediate Similarity	NPC186688
0.8172	Intermediate Similarity	NPC112167
0.8172	Intermediate Similarity	NPC472972
0.8171	Intermediate Similarity	NPC471409
0.8171	Intermediate Similarity	NPC275494
0.8171	Intermediate Similarity	NPC476949
0.8161	Intermediate Similarity	NPC471792
0.8161	Intermediate Similarity	NPC73064
0.8161	Intermediate Similarity	NPC58063
0.8148	Intermediate Similarity	NPC167873
0.8148	Intermediate Similarity	NPC7629
0.8148	Intermediate Similarity	NPC151622
0.8148	Intermediate Similarity	NPC1973
0.814	Intermediate Similarity	NPC476426
0.814	Intermediate Similarity	NPC79573
0.814	Intermediate Similarity	NPC202868
0.814	Intermediate Similarity	NPC36350
0.814	Intermediate Similarity	NPC469948
0.8132	Intermediate Similarity	NPC470016
0.8132	Intermediate Similarity	NPC148523
0.8132	Intermediate Similarity	NPC271195
0.8132	Intermediate Similarity	NPC477437
0.8132	Intermediate Similarity	NPC474602
0.8132	Intermediate Similarity	NPC317586
0.8132	Intermediate Similarity	NPC477438
0.8132	Intermediate Similarity	NPC272617
0.8132	Intermediate Similarity	NPC180950
0.8111	Intermediate Similarity	NPC295643
0.8111	Intermediate Similarity	NPC272075
0.8111	Intermediate Similarity	NPC134826
0.8111	Intermediate Similarity	NPC475255
0.8111	Intermediate Similarity	NPC214756
0.8101	Intermediate Similarity	NPC164022
0.8095	Intermediate Similarity	NPC116797
0.8095	Intermediate Similarity	NPC136150
0.8095	Intermediate Similarity	NPC14151
0.809	Intermediate Similarity	NPC48010
0.809	Intermediate Similarity	NPC472325
0.809	Intermediate Similarity	NPC126993
0.8072	Intermediate Similarity	NPC152061
0.8072	Intermediate Similarity	NPC229204
0.8068	Intermediate Similarity	NPC471724
0.8068	Intermediate Similarity	NPC474677
0.8068	Intermediate Similarity	NPC104560
0.8068	Intermediate Similarity	NPC471941
0.8068	Intermediate Similarity	NPC53911
0.8068	Intermediate Similarity	NPC193360
0.8065	Intermediate Similarity	NPC114274
0.8049	Intermediate Similarity	NPC203403
0.8049	Intermediate Similarity	NPC470428
0.8046	Intermediate Similarity	NPC118648
0.8046	Intermediate Similarity	NPC235341

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 NPC64600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1698
0.2-0.3	3932
0.3-0.4	2251
0.4-0.5	665
0.5-0.6	186
0.6-0.7	142
0.7-0.8	102
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD5328	Approved
0.869	High Similarity	NPD3618	Phase 1
0.8621	High Similarity	NPD6079	Approved
0.8556	High Similarity	NPD4755	Approved
0.837	Intermediate Similarity	NPD5286	Approved
0.837	Intermediate Similarity	NPD4696	Approved
0.837	Intermediate Similarity	NPD4700	Approved
0.837	Intermediate Similarity	NPD5285	Approved
0.8315	Intermediate Similarity	NPD4202	Approved
0.8242	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4697	Phase 3
0.8242	Intermediate Similarity	NPD5221	Approved
0.8242	Intermediate Similarity	NPD5222	Approved
0.8235	Intermediate Similarity	NPD3133	Approved
0.8235	Intermediate Similarity	NPD3665	Phase 1
0.8235	Intermediate Similarity	NPD3666	Approved
0.8214	Intermediate Similarity	NPD3667	Approved
0.8202	Intermediate Similarity	NPD7515	Phase 2
0.8191	Intermediate Similarity	NPD5225	Approved
0.8191	Intermediate Similarity	NPD5224	Approved
0.8191	Intermediate Similarity	NPD5226	Approved
0.8191	Intermediate Similarity	NPD4633	Approved
0.8191	Intermediate Similarity	NPD5211	Phase 2
0.8152	Intermediate Similarity	NPD5173	Approved
0.8105	Intermediate Similarity	NPD5174	Approved
0.8105	Intermediate Similarity	NPD5175	Approved
0.8085	Intermediate Similarity	NPD5223	Approved
0.8023	Intermediate Similarity	NPD4786	Approved
0.8021	Intermediate Similarity	NPD5141	Approved
0.7978	Intermediate Similarity	NPD4753	Phase 2
0.7938	Intermediate Similarity	NPD5739	Approved
0.7938	Intermediate Similarity	NPD7128	Approved
0.7938	Intermediate Similarity	NPD4767	Approved
0.7938	Intermediate Similarity	NPD4768	Approved
0.7938	Intermediate Similarity	NPD6675	Approved
0.7938	Intermediate Similarity	NPD6402	Approved
0.7917	Intermediate Similarity	NPD4754	Approved
0.7857	Intermediate Similarity	NPD5697	Approved
0.7857	Intermediate Similarity	NPD5701	Approved
0.7841	Intermediate Similarity	NPD5279	Phase 3
0.7826	Intermediate Similarity	NPD7748	Approved
0.7791	Intermediate Similarity	NPD4221	Approved
0.7791	Intermediate Similarity	NPD4223	Phase 3
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD5128	Approved
0.7778	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD4730	Approved
0.7778	Intermediate Similarity	NPD4729	Approved
0.7778	Intermediate Similarity	NPD6899	Approved
0.7753	Intermediate Similarity	NPD3573	Approved
0.77	Intermediate Similarity	NPD6013	Approved
0.77	Intermediate Similarity	NPD6373	Approved
0.77	Intermediate Similarity	NPD6372	Approved
0.77	Intermediate Similarity	NPD6012	Approved
0.77	Intermediate Similarity	NPD6014	Approved
0.764	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5248	Approved
0.7624	Intermediate Similarity	NPD7102	Approved
0.7624	Intermediate Similarity	NPD5247	Approved
0.7624	Intermediate Similarity	NPD4634	Approved
0.7624	Intermediate Similarity	NPD5251	Approved
0.7624	Intermediate Similarity	NPD7290	Approved
0.7624	Intermediate Similarity	NPD6883	Approved
0.7624	Intermediate Similarity	NPD5250	Approved
0.7624	Intermediate Similarity	NPD5249	Phase 3
0.7614	Intermediate Similarity	NPD4197	Approved
0.76	Intermediate Similarity	NPD6011	Approved
0.7579	Intermediate Similarity	NPD7902	Approved
0.7558	Intermediate Similarity	NPD4695	Discontinued
0.7553	Intermediate Similarity	NPD5210	Approved
0.7553	Intermediate Similarity	NPD4629	Approved
0.7549	Intermediate Similarity	NPD6617	Approved
0.7549	Intermediate Similarity	NPD5216	Approved
0.7549	Intermediate Similarity	NPD6650	Approved
0.7549	Intermediate Similarity	NPD6869	Approved
0.7549	Intermediate Similarity	NPD6649	Approved
0.7549	Intermediate Similarity	NPD6847	Approved
0.7549	Intermediate Similarity	NPD8130	Phase 1
0.7549	Intermediate Similarity	NPD5217	Approved
0.7549	Intermediate Similarity	NPD5215	Approved
0.7528	Intermediate Similarity	NPD5329	Approved
0.7476	Intermediate Similarity	NPD6882	Approved
0.7476	Intermediate Similarity	NPD8297	Approved
0.7468	Intermediate Similarity	NPD7331	Phase 2
0.7451	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5169	Approved
0.7451	Intermediate Similarity	NPD5135	Approved
0.7444	Intermediate Similarity	NPD5280	Approved
0.7444	Intermediate Similarity	NPD4623	Approved
0.7444	Intermediate Similarity	NPD4690	Approved
0.7444	Intermediate Similarity	NPD4693	Phase 3
0.7444	Intermediate Similarity	NPD4694	Approved
0.7444	Intermediate Similarity	NPD4519	Discontinued
0.7444	Intermediate Similarity	NPD4688	Approved
0.7444	Intermediate Similarity	NPD5205	Approved
0.7444	Intermediate Similarity	NPD4138	Approved
0.7444	Intermediate Similarity	NPD4689	Approved
0.7444	Intermediate Similarity	NPD5690	Phase 2
0.7442	Intermediate Similarity	NPD7645	Phase 2
0.7426	Intermediate Similarity	NPD5168	Approved
0.7416	Intermediate Similarity	NPD3668	Phase 3
0.7396	Intermediate Similarity	NPD6084	Phase 2
0.7396	Intermediate Similarity	NPD6083	Phase 2
0.7379	Intermediate Similarity	NPD5127	Approved
0.7379	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5695	Phase 3
0.7342	Intermediate Similarity	NPD7341	Phase 2
0.7333	Intermediate Similarity	NPD1696	Phase 3
0.7326	Intermediate Similarity	NPD3617	Approved
0.7264	Intermediate Similarity	NPD6274	Approved
0.7263	Intermediate Similarity	NPD7900	Approved
0.7263	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7238	Intermediate Similarity	NPD4632	Approved
0.7234	Intermediate Similarity	NPD6411	Approved
0.717	Intermediate Similarity	NPD5167	Approved
0.7159	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7525	Registered
0.7158	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4788	Approved
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6903	Approved
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7100	Approved
0.7064	Intermediate Similarity	NPD7101	Approved
0.7059	Intermediate Similarity	NPD6008	Approved
0.7053	Intermediate Similarity	NPD5284	Approved
0.7053	Intermediate Similarity	NPD5281	Approved
0.7045	Intermediate Similarity	NPD4195	Approved
0.7037	Intermediate Similarity	NPD6009	Approved
0.7037	Intermediate Similarity	NPD6317	Approved
0.7021	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD6054	Approved
0.6988	Remote Similarity	NPD4137	Phase 3
0.6977	Remote Similarity	NPD7339	Approved
0.6977	Remote Similarity	NPD3703	Phase 2
0.6977	Remote Similarity	NPD6942	Approved
0.6972	Remote Similarity	NPD6314	Approved
0.6972	Remote Similarity	NPD6335	Approved
0.6972	Remote Similarity	NPD6313	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD4096	Approved
0.6944	Remote Similarity	NPD6868	Approved
0.6937	Remote Similarity	NPD6015	Approved
0.6937	Remote Similarity	NPD6016	Approved
0.6937	Remote Similarity	NPD6909	Approved
0.6937	Remote Similarity	NPD6908	Approved
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6672	Approved
0.6905	Remote Similarity	NPD4747	Approved
0.6905	Remote Similarity	NPD4691	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6889	Remote Similarity	NPD4139	Approved
0.6889	Remote Similarity	NPD4692	Approved
0.6881	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD6370	Approved
0.6875	Remote Similarity	NPD5988	Approved
0.6842	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6412	Phase 2
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5133	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.68	Remote Similarity	NPD4225	Approved
0.68	Remote Similarity	NPD5290	Discontinued
0.6786	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5983	Phase 2
0.6786	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7492	Approved
0.6737	Remote Similarity	NPD4518	Approved
0.6737	Remote Similarity	NPD5208	Approved
0.6735	Remote Similarity	NPD6001	Approved
0.6698	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD4058	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6638	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD8293	Discontinued

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