NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	280.771
LogP:	0.812
LogD:	0.731
LogS:	-1.326
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	4.705
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:	-5.025
MDCK Permeability:	1.893995977297891e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.526
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.675
Plasma Protein Binding (PPB):	50.22691345214844%
Volume Distribution (VD):	0.356
Pgp-substrate:	34.836788177490234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.775
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.709

ADMET: Excretion

Clearance (CL):	3.669
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.723
Drug-inuced Liver Injury (DILI):	0.153
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.863
Carcinogencity:	0.954
Eye Corrosion:	0.046
Eye Irritation:	0.597
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC134321

Natural Product ID:	NPC134321
*Common Name:**	Kandenol B
IUPAC Name:	(4aS,6R,7R,8aS)-4a,7-dihydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-5,6,7,8-tetrahydro-1H-naphthalen-2-one
Synonyms:	Kandenol B
Standard InCHIKey:	FJPRABNPMYDAOJ-QHSBEEBCSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-9-5-10(16)6-14(4)8-12(17)11(13(2,3)18)7-15(9,14)19/h5,11-12,17-19H,6-8H2,1-4H3/t11-,12-,14-,15-/m1/s1
SMILES:	CC1=CC(=O)C[C@]2(C)C[C@H]([C@@H](C[C@@]12O)C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208381
PubChem CID:	71459823
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[474946]
NPT3473	Organism	Mycobacterium vaccae	Mycobacterium vaccae	MIC	=	12.5	ug.mL-1	PMID[474946]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[474946]

☑ 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 NPC134321 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	191
0.1-0.2	1209
0.2-0.3	4517
0.3-0.4	8844
0.4-0.5	13690
0.5-0.6	7199
0.6-0.7	5217
0.7-0.8	1692
0.8-0.85	117
0.85-0.9	18
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC128672
0.9213	High Similarity	NPC196227
0.9167	High Similarity	NPC64600
0.9111	High Similarity	NPC316215
0.9059	High Similarity	NPC40687
0.8989	High Similarity	NPC116726
0.8989	High Similarity	NPC472978
0.881	High Similarity	NPC172013
0.8791	High Similarity	NPC103527
0.8764	High Similarity	NPC472973
0.8764	High Similarity	NPC472983
0.8721	High Similarity	NPC105173
0.8706	High Similarity	NPC226068
0.8696	High Similarity	NPC476245
0.869	High Similarity	NPC308038
0.8667	High Similarity	NPC230332
0.8605	High Similarity	NPC93590
0.8602	High Similarity	NPC249954
0.8587	High Similarity	NPC472977
0.8587	High Similarity	NPC472976
0.8495	Intermediate Similarity	NPC259286
0.8495	Intermediate Similarity	NPC272617
0.8495	Intermediate Similarity	NPC134067
0.8478	Intermediate Similarity	NPC69454
0.8478	Intermediate Similarity	NPC472930
0.8471	Intermediate Similarity	NPC281138
0.8462	Intermediate Similarity	NPC473099
0.8452	Intermediate Similarity	NPC197659
0.8452	Intermediate Similarity	NPC266193
0.8452	Intermediate Similarity	NPC257666
0.8452	Intermediate Similarity	NPC34110
0.8427	Intermediate Similarity	NPC472974
0.8427	Intermediate Similarity	NPC472985
0.8427	Intermediate Similarity	NPC472986
0.8427	Intermediate Similarity	NPC473226
0.8409	Intermediate Similarity	NPC251170
0.8409	Intermediate Similarity	NPC470812
0.8384	Intermediate Similarity	NPC83744
0.8372	Intermediate Similarity	NPC104120
0.8372	Intermediate Similarity	NPC148685
0.8372	Intermediate Similarity	NPC157895
0.837	Intermediate Similarity	NPC472975
0.837	Intermediate Similarity	NPC63748
0.837	Intermediate Similarity	NPC172101
0.837	Intermediate Similarity	NPC475441
0.8367	Intermediate Similarity	NPC118911
0.8353	Intermediate Similarity	NPC62336
0.8352	Intermediate Similarity	NPC473100
0.8351	Intermediate Similarity	NPC477915
0.8333	Intermediate Similarity	NPC151622
0.8333	Intermediate Similarity	NPC263582
0.8333	Intermediate Similarity	NPC7629
0.8333	Intermediate Similarity	NPC472305
0.8333	Intermediate Similarity	NPC154072
0.8333	Intermediate Similarity	NPC471792
0.8333	Intermediate Similarity	NPC476274
0.8316	Intermediate Similarity	NPC18509
0.8316	Intermediate Similarity	NPC254496
0.8315	Intermediate Similarity	NPC476426
0.83	Intermediate Similarity	NPC217201
0.83	Intermediate Similarity	NPC329417
0.8298	Intermediate Similarity	NPC271195
0.8298	Intermediate Similarity	NPC473170
0.8298	Intermediate Similarity	NPC266899
0.8298	Intermediate Similarity	NPC180950
0.8295	Intermediate Similarity	NPC66764
0.8295	Intermediate Similarity	NPC251475
0.8295	Intermediate Similarity	NPC169941
0.8295	Intermediate Similarity	NPC110150
0.8283	Intermediate Similarity	NPC50692
0.8283	Intermediate Similarity	NPC49958
0.8283	Intermediate Similarity	NPC260268
0.8283	Intermediate Similarity	NPC302607
0.8283	Intermediate Similarity	NPC476027
0.8283	Intermediate Similarity	NPC152695
0.8283	Intermediate Similarity	NPC48733
0.8283	Intermediate Similarity	NPC202167
0.8283	Intermediate Similarity	NPC296945
0.8283	Intermediate Similarity	NPC85829
0.8283	Intermediate Similarity	NPC171137
0.8283	Intermediate Similarity	NPC150531
0.8283	Intermediate Similarity	NPC214264
0.8283	Intermediate Similarity	NPC319077
0.8283	Intermediate Similarity	NPC97202
0.8247	Intermediate Similarity	NPC81530
0.8247	Intermediate Similarity	NPC115862
0.8247	Intermediate Similarity	NPC472637
0.8247	Intermediate Similarity	NPC476223
0.8247	Intermediate Similarity	NPC470184
0.8247	Intermediate Similarity	NPC224720
0.8247	Intermediate Similarity	NPC476240
0.8242	Intermediate Similarity	NPC48107
0.8242	Intermediate Similarity	NPC328539
0.8242	Intermediate Similarity	NPC471791
0.8242	Intermediate Similarity	NPC104560
0.8242	Intermediate Similarity	NPC471793
0.8235	Intermediate Similarity	NPC74995
0.8218	Intermediate Similarity	NPC11710
0.8211	Intermediate Similarity	NPC117133
0.8202	Intermediate Similarity	NPC476412
0.82	Intermediate Similarity	NPC220229
0.82	Intermediate Similarity	NPC477916
0.82	Intermediate Similarity	NPC475060
0.8191	Intermediate Similarity	NPC299100
0.8191	Intermediate Similarity	NPC8993
0.8191	Intermediate Similarity	NPC474690
0.8182	Intermediate Similarity	NPC209502
0.8182	Intermediate Similarity	NPC204833
0.8182	Intermediate Similarity	NPC279186
0.8172	Intermediate Similarity	NPC473998
0.8172	Intermediate Similarity	NPC99380
0.8172	Intermediate Similarity	NPC73457
0.8172	Intermediate Similarity	NPC475806
0.8172	Intermediate Similarity	NPC168027
0.8172	Intermediate Similarity	NPC185936
0.8172	Intermediate Similarity	NPC252433
0.8163	Intermediate Similarity	NPC136289
0.8163	Intermediate Similarity	NPC473424
0.8161	Intermediate Similarity	NPC472301
0.8152	Intermediate Similarity	NPC275740
0.8152	Intermediate Similarity	NPC309603
0.8152	Intermediate Similarity	NPC473999
0.8152	Intermediate Similarity	NPC86319
0.8144	Intermediate Similarity	NPC198880
0.8144	Intermediate Similarity	NPC144956
0.8125	Intermediate Similarity	NPC285513
0.8125	Intermediate Similarity	NPC170131
0.8125	Intermediate Similarity	NPC474785
0.8125	Intermediate Similarity	NPC474938
0.8119	Intermediate Similarity	NPC65941
0.8118	Intermediate Similarity	NPC186554
0.8118	Intermediate Similarity	NPC76966
0.8105	Intermediate Similarity	NPC472932
0.8105	Intermediate Similarity	NPC139570
0.8105	Intermediate Similarity	NPC53565
0.81	Intermediate Similarity	NPC472645
0.81	Intermediate Similarity	NPC149047
0.81	Intermediate Similarity	NPC85529
0.81	Intermediate Similarity	NPC1679
0.81	Intermediate Similarity	NPC32006
0.809	Intermediate Similarity	NPC243347
0.809	Intermediate Similarity	NPC297398
0.8085	Intermediate Similarity	NPC477435
0.8085	Intermediate Similarity	NPC477436
0.8081	Intermediate Similarity	NPC478057
0.8081	Intermediate Similarity	NPC247957
0.8081	Intermediate Similarity	NPC249187
0.8081	Intermediate Similarity	NPC311612
0.8081	Intermediate Similarity	NPC473624
0.8077	Intermediate Similarity	NPC108721
0.8077	Intermediate Similarity	NPC73300
0.8068	Intermediate Similarity	NPC119229
0.8065	Intermediate Similarity	NPC48010
0.8061	Intermediate Similarity	NPC207885
0.8061	Intermediate Similarity	NPC302537
0.8061	Intermediate Similarity	NPC163372
0.8061	Intermediate Similarity	NPC112613
0.8046	Intermediate Similarity	NPC152061
0.8043	Intermediate Similarity	NPC158778
0.8043	Intermediate Similarity	NPC472802
0.8043	Intermediate Similarity	NPC143767
0.8043	Intermediate Similarity	NPC131470
0.8043	Intermediate Similarity	NPC473229
0.8041	Intermediate Similarity	NPC478056
0.8039	Intermediate Similarity	NPC214644
0.8023	Intermediate Similarity	NPC203403
0.8023	Intermediate Similarity	NPC85105
0.8023	Intermediate Similarity	NPC149550
0.8022	Intermediate Similarity	NPC179591
0.8022	Intermediate Similarity	NPC470955
0.8022	Intermediate Similarity	NPC476043
0.8022	Intermediate Similarity	NPC194417
0.8022	Intermediate Similarity	NPC198761
0.8022	Intermediate Similarity	NPC94666
0.8021	Intermediate Similarity	NPC469545
0.8021	Intermediate Similarity	NPC5532
0.8021	Intermediate Similarity	NPC192428
0.8021	Intermediate Similarity	NPC116457
0.8021	Intermediate Similarity	NPC61369
0.802	Intermediate Similarity	NPC185
0.8	Intermediate Similarity	NPC474281
0.8	Intermediate Similarity	NPC227132
0.8	Intermediate Similarity	NPC72255
0.7981	Intermediate Similarity	NPC472002
0.7981	Intermediate Similarity	NPC207251
0.798	Intermediate Similarity	NPC87351
0.798	Intermediate Similarity	NPC204450
0.798	Intermediate Similarity	NPC195290
0.798	Intermediate Similarity	NPC119601
0.798	Intermediate Similarity	NPC308726
0.7979	Intermediate Similarity	NPC233116
0.7976	Intermediate Similarity	NPC247586
0.7959	Intermediate Similarity	NPC287833
0.7959	Intermediate Similarity	NPC46761
0.7959	Intermediate Similarity	NPC472644
0.7959	Intermediate Similarity	NPC51370
0.7957	Intermediate Similarity	NPC472676
0.7957	Intermediate Similarity	NPC36668
0.7957	Intermediate Similarity	NPC123912
0.7957	Intermediate Similarity	NPC472970

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 NPC134321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1681
0.2-0.3	3750
0.3-0.4	2331
0.4-0.5	761
0.5-0.6	214
0.6-0.7	157
0.7-0.8	82
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
0.8351	Intermediate Similarity	NPD5211	Phase 2
0.8316	Intermediate Similarity	NPD4755	Approved
0.8222	Intermediate Similarity	NPD3618	Phase 1
0.8182	Intermediate Similarity	NPD5141	Approved
0.8152	Intermediate Similarity	NPD5328	Approved
0.8144	Intermediate Similarity	NPD5285	Approved
0.8144	Intermediate Similarity	NPD5286	Approved
0.8144	Intermediate Similarity	NPD4700	Approved
0.8144	Intermediate Similarity	NPD4696	Approved
0.8021	Intermediate Similarity	NPD4697	Phase 3
0.798	Intermediate Similarity	NPD5224	Approved
0.798	Intermediate Similarity	NPD5225	Approved
0.798	Intermediate Similarity	NPD4633	Approved
0.798	Intermediate Similarity	NPD5226	Approved
0.7979	Intermediate Similarity	NPD6079	Approved
0.79	Intermediate Similarity	NPD5175	Approved
0.79	Intermediate Similarity	NPD5174	Approved
0.7895	Intermediate Similarity	NPD4202	Approved
0.7879	Intermediate Similarity	NPD5223	Approved
0.7835	Intermediate Similarity	NPD5222	Approved
0.7835	Intermediate Similarity	NPD5221	Approved
0.7835	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7515	Phase 2
0.7755	Intermediate Similarity	NPD5173	Approved
0.7745	Intermediate Similarity	NPD6402	Approved
0.7745	Intermediate Similarity	NPD5739	Approved
0.7745	Intermediate Similarity	NPD7128	Approved
0.7745	Intermediate Similarity	NPD4767	Approved
0.7745	Intermediate Similarity	NPD4768	Approved
0.7745	Intermediate Similarity	NPD6675	Approved
0.7723	Intermediate Similarity	NPD4754	Approved
0.7692	Intermediate Similarity	NPD6372	Approved
0.7692	Intermediate Similarity	NPD6373	Approved
0.767	Intermediate Similarity	NPD5697	Approved
0.767	Intermediate Similarity	NPD5701	Approved
0.7609	Intermediate Similarity	NPD3666	Approved
0.7609	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD3133	Approved
0.7596	Intermediate Similarity	NPD4729	Approved
0.7596	Intermediate Similarity	NPD6881	Approved
0.7596	Intermediate Similarity	NPD5128	Approved
0.7596	Intermediate Similarity	NPD7320	Approved
0.7596	Intermediate Similarity	NPD6899	Approved
0.7596	Intermediate Similarity	NPD4730	Approved
0.7582	Intermediate Similarity	NPD3667	Approved
0.7579	Intermediate Similarity	NPD4753	Phase 2
0.7576	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD6650	Approved
0.7547	Intermediate Similarity	NPD6649	Approved
0.7524	Intermediate Similarity	NPD6013	Approved
0.7524	Intermediate Similarity	NPD6014	Approved
0.7524	Intermediate Similarity	NPD6012	Approved
0.7453	Intermediate Similarity	NPD5251	Approved
0.7453	Intermediate Similarity	NPD5250	Approved
0.7453	Intermediate Similarity	NPD4634	Approved
0.7453	Intermediate Similarity	NPD7102	Approved
0.7453	Intermediate Similarity	NPD5249	Phase 3
0.7453	Intermediate Similarity	NPD5248	Approved
0.7453	Intermediate Similarity	NPD5247	Approved
0.7453	Intermediate Similarity	NPD6883	Approved
0.7453	Intermediate Similarity	NPD7290	Approved
0.7449	Intermediate Similarity	NPD7748	Approved
0.7447	Intermediate Similarity	NPD4623	Approved
0.7447	Intermediate Similarity	NPD4519	Discontinued
0.7447	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6011	Approved
0.7419	Intermediate Similarity	NPD4786	Approved
0.7383	Intermediate Similarity	NPD5217	Approved
0.7383	Intermediate Similarity	NPD6847	Approved
0.7383	Intermediate Similarity	NPD5216	Approved
0.7383	Intermediate Similarity	NPD6617	Approved
0.7383	Intermediate Similarity	NPD6869	Approved
0.7383	Intermediate Similarity	NPD8130	Phase 1
0.7383	Intermediate Similarity	NPD5215	Approved
0.7374	Intermediate Similarity	NPD5210	Approved
0.7374	Intermediate Similarity	NPD4629	Approved
0.734	Intermediate Similarity	NPD1696	Phase 3
0.7315	Intermediate Similarity	NPD8297	Approved
0.7315	Intermediate Similarity	NPD6882	Approved
0.729	Intermediate Similarity	NPD5169	Approved
0.729	Intermediate Similarity	NPD5135	Approved
0.729	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5279	Phase 3
0.7222	Intermediate Similarity	NPD5127	Approved
0.7222	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7204	Intermediate Similarity	NPD4221	Approved
0.7204	Intermediate Similarity	NPD4223	Phase 3
0.7188	Intermediate Similarity	NPD3573	Approved
0.7174	Intermediate Similarity	NPD4695	Discontinued
0.7172	Intermediate Similarity	NPD6399	Phase 3
0.7158	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD4225	Approved
0.7117	Intermediate Similarity	NPD6274	Approved
0.7103	Intermediate Similarity	NPD5168	Approved
0.7091	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD7640	Approved
0.7075	Intermediate Similarity	NPD6008	Approved
0.7071	Intermediate Similarity	NPD5281	Approved
0.7071	Intermediate Similarity	NPD5284	Approved
0.7059	Intermediate Similarity	NPD6084	Phase 2
0.7059	Intermediate Similarity	NPD6083	Phase 2
0.7053	Intermediate Similarity	NPD4197	Approved
0.7053	Intermediate Similarity	NPD3668	Phase 3
0.7037	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5695	Phase 3
0.7027	Intermediate Similarity	NPD5167	Approved
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.699	Remote Similarity	NPD5696	Approved
0.699	Remote Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD7525	Registered
0.6979	Remote Similarity	NPD5329	Approved
0.6972	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7101	Approved
0.693	Remote Similarity	NPD7100	Approved
0.6907	Remote Similarity	NPD4694	Approved
0.6907	Remote Similarity	NPD4689	Approved
0.6907	Remote Similarity	NPD4693	Phase 3
0.6907	Remote Similarity	NPD5280	Approved
0.6907	Remote Similarity	NPD4138	Approved
0.6907	Remote Similarity	NPD4690	Approved
0.6907	Remote Similarity	NPD5205	Approved
0.6907	Remote Similarity	NPD4688	Approved
0.6907	Remote Similarity	NPD5690	Phase 2
0.6903	Remote Similarity	NPD6317	Approved
0.6903	Remote Similarity	NPD6009	Approved
0.69	Remote Similarity	NPD6411	Approved
0.6882	Remote Similarity	NPD7645	Phase 2
0.687	Remote Similarity	NPD6319	Approved
0.687	Remote Similarity	NPD6054	Approved
0.687	Remote Similarity	NPD6059	Approved
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7331	Phase 2
0.6842	Remote Similarity	NPD6313	Approved
0.6842	Remote Similarity	NPD6314	Approved
0.6842	Remote Similarity	NPD6335	Approved
0.681	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD6015	Approved
0.681	Remote Similarity	NPD6909	Approved
0.681	Remote Similarity	NPD6016	Approved
0.6809	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD368	Approved
0.6774	Remote Similarity	NPD3617	Approved
0.6752	Remote Similarity	NPD6370	Approved
0.6752	Remote Similarity	NPD5988	Approved
0.6744	Remote Similarity	NPD7341	Phase 2
0.6735	Remote Similarity	NPD6409	Approved
0.6735	Remote Similarity	NPD5330	Approved
0.6735	Remote Similarity	NPD7521	Approved
0.6735	Remote Similarity	NPD6684	Approved
0.6735	Remote Similarity	NPD7334	Approved
0.6735	Remote Similarity	NPD7146	Approved
0.67	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6101	Approved
0.6699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD7492	Approved
0.6633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8264	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.66	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6903	Approved
0.66	Remote Similarity	NPD5737	Approved
0.66	Remote Similarity	NPD6672	Approved
0.6598	Remote Similarity	NPD4788	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6616	Approved
0.6583	Remote Similarity	NPD7507	Approved
0.6569	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6559	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD6053	Discontinued
0.6535	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8293	Discontinued
0.6529	Remote Similarity	NPD7078	Approved
0.6526	Remote Similarity	NPD4195	Approved
0.65	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6686	Approved
0.6481	Remote Similarity	NPD7632	Discontinued
0.6475	Remote Similarity	NPD7736	Approved
0.6471	Remote Similarity	NPD4096	Approved
0.6471	Remote Similarity	NPD5785	Approved
0.6465	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD5368	Approved
0.6452	Remote Similarity	NPD7339	Approved
0.6452	Remote Similarity	NPD3703	Phase 2
0.6452	Remote Similarity	NPD6942	Approved
0.6446	Remote Similarity	NPD6336	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