NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	280.771
LogP:	1.697
LogD:	1.192
LogS:	-1.7
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	4.552
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.796
MDCK Permeability:	1.3395482710620854e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	74.71671295166016%
Volume Distribution (VD):	0.421
Pgp-substrate:	20.30544090270996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.826
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.712

ADMET: Excretion

Clearance (CL):	7.89
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.751
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.892
Carcinogencity:	0.941
Eye Corrosion:	0.569
Eye Irritation:	0.752
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC226068

Natural Product ID:	NPC226068
*Common Name:**	Kandenol D
IUPAC Name:	(4aS,6S,8aS)-4a-hydroperoxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-5,6,7,8-tetrahydro-1H-naphthalen-2-one
Synonyms:	Kandenol D
Standard InCHIKey:	XPVKEIHKYHPNSX-TUKIKUTGSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-10-7-12(16)9-14(4)6-5-11(13(2,3)17)8-15(10,14)19-18/h7,11,17-18H,5-6,8-9H2,1-4H3/t11-,14-,15+/m0/s1
SMILES:	CC1=CC(=O)C[C@]2(C)CC[C@@H](C[C@@]12OO)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208378
PubChem CID:	71452597
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[493702]
NPT3473	Organism	Mycobacterium vaccae	Mycobacterium vaccae	MIC	=	25.0	ug.mL-1	PMID[493702]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[493702]

☑ 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 NPC226068 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	178
0.1-0.2	1228
0.2-0.3	5257
0.3-0.4	12957
0.4-0.5	11115
0.5-0.6	6870
0.6-0.7	4029
0.7-0.8	981
0.8-0.85	67
0.85-0.9	13
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC34110
0.8961	High Similarity	NPC257666
0.8961	High Similarity	NPC266193
0.8929	High Similarity	NPC128672
0.8831	High Similarity	NPC186554
0.8831	High Similarity	NPC7629
0.8831	High Similarity	NPC472305
0.8831	High Similarity	NPC76966
0.8831	High Similarity	NPC151622
0.8706	High Similarity	NPC134321
0.869	High Similarity	NPC48107
0.8684	High Similarity	NPC247586
0.8625	High Similarity	NPC172013
0.8608	High Similarity	NPC275494
0.8608	High Similarity	NPC471409
0.85	High Similarity	NPC308038
0.8481	Intermediate Similarity	NPC197659
0.8434	Intermediate Similarity	NPC251170
0.8409	Intermediate Similarity	NPC196227
0.8395	Intermediate Similarity	NPC476809
0.8395	Intermediate Similarity	NPC472301
0.8395	Intermediate Similarity	NPC469637
0.8391	Intermediate Similarity	NPC116726
0.8375	Intermediate Similarity	NPC207772
0.8372	Intermediate Similarity	NPC472983
0.8354	Intermediate Similarity	NPC263582
0.8354	Intermediate Similarity	NPC180886
0.8353	Intermediate Similarity	NPC471792
0.8313	Intermediate Similarity	NPC297398
0.8313	Intermediate Similarity	NPC64600
0.8293	Intermediate Similarity	NPC473217
0.8272	Intermediate Similarity	NPC170394
0.8272	Intermediate Similarity	NPC281138
0.8256	Intermediate Similarity	NPC471793
0.8256	Intermediate Similarity	NPC471791
0.825	Intermediate Similarity	NPC97377
0.8193	Intermediate Similarity	NPC92226
0.8193	Intermediate Similarity	NPC93590
0.8171	Intermediate Similarity	NPC824
0.8171	Intermediate Similarity	NPC148685
0.8171	Intermediate Similarity	NPC138492
0.8171	Intermediate Similarity	NPC233352
0.8171	Intermediate Similarity	NPC104120
0.8171	Intermediate Similarity	NPC157895
0.8161	Intermediate Similarity	NPC472688
0.8161	Intermediate Similarity	NPC118011
0.8161	Intermediate Similarity	NPC472676
0.8161	Intermediate Similarity	NPC36668
0.8148	Intermediate Similarity	NPC62336
0.8148	Intermediate Similarity	NPC253561
0.8148	Intermediate Similarity	NPC74410
0.8148	Intermediate Similarity	NPC80088
0.8148	Intermediate Similarity	NPC19443
0.814	Intermediate Similarity	NPC181327
0.8111	Intermediate Similarity	NPC316215
0.8111	Intermediate Similarity	NPC476245
0.8095	Intermediate Similarity	NPC49019
0.8077	Intermediate Similarity	NPC84790
0.8072	Intermediate Similarity	NPC472684
0.8072	Intermediate Similarity	NPC278459
0.8072	Intermediate Similarity	NPC44963
0.8072	Intermediate Similarity	NPC55869
0.8068	Intermediate Similarity	NPC230332
0.8046	Intermediate Similarity	NPC72397
0.8026	Intermediate Similarity	NPC263161
0.8025	Intermediate Similarity	NPC74995
0.8025	Intermediate Similarity	NPC61952
0.8025	Intermediate Similarity	NPC165711
0.8023	Intermediate Similarity	NPC473226
0.8023	Intermediate Similarity	NPC470415
0.8023	Intermediate Similarity	NPC472974
0.8023	Intermediate Similarity	NPC472985
0.8023	Intermediate Similarity	NPC472986
0.8	Intermediate Similarity	NPC8993
0.8	Intermediate Similarity	NPC470812
0.8	Intermediate Similarity	NPC40687
0.8	Intermediate Similarity	NPC476795
0.8	Intermediate Similarity	NPC476412
0.7978	Intermediate Similarity	NPC472978
0.7978	Intermediate Similarity	NPC473998
0.7978	Intermediate Similarity	NPC252433
0.7976	Intermediate Similarity	NPC193347
0.7957	Intermediate Similarity	NPC154072
0.7955	Intermediate Similarity	NPC474918
0.7955	Intermediate Similarity	NPC472973
0.7952	Intermediate Similarity	NPC108955
0.7952	Intermediate Similarity	NPC2482
0.7935	Intermediate Similarity	NPC170131
0.7931	Intermediate Similarity	NPC476409
0.7931	Intermediate Similarity	NPC136948
0.7927	Intermediate Similarity	NPC189485
0.7927	Intermediate Similarity	NPC179028
0.7927	Intermediate Similarity	NPC198240
0.7927	Intermediate Similarity	NPC476808
0.7927	Intermediate Similarity	NPC321514
0.7912	Intermediate Similarity	NPC147232
0.7912	Intermediate Similarity	NPC271195
0.7907	Intermediate Similarity	NPC476426
0.7907	Intermediate Similarity	NPC70685
0.7901	Intermediate Similarity	NPC470525
0.7895	Intermediate Similarity	NPC103734
0.7889	Intermediate Similarity	NPC476416
0.7882	Intermediate Similarity	NPC97913
0.7882	Intermediate Similarity	NPC169941
0.7882	Intermediate Similarity	NPC105173
0.7882	Intermediate Similarity	NPC251475
0.7875	Intermediate Similarity	NPC470299
0.7865	Intermediate Similarity	NPC473099
0.7857	Intermediate Similarity	NPC189237
0.7857	Intermediate Similarity	NPC116797
0.7857	Intermediate Similarity	NPC121984
0.7857	Intermediate Similarity	NPC471898
0.7857	Intermediate Similarity	NPC477372
0.7857	Intermediate Similarity	NPC119229
0.7841	Intermediate Similarity	NPC476427
0.7841	Intermediate Similarity	NPC58271
0.7841	Intermediate Similarity	NPC472802
0.7841	Intermediate Similarity	NPC473229
0.7841	Intermediate Similarity	NPC475101
0.7841	Intermediate Similarity	NPC124927
0.7831	Intermediate Similarity	NPC152061
0.7826	Intermediate Similarity	NPC249954
0.7826	Intermediate Similarity	NPC117133
0.7821	Intermediate Similarity	NPC136473
0.7816	Intermediate Similarity	NPC470955
0.7816	Intermediate Similarity	NPC179591
0.7816	Intermediate Similarity	NPC472869
0.7816	Intermediate Similarity	NPC198761
0.7816	Intermediate Similarity	NPC194417
0.7805	Intermediate Similarity	NPC132542
0.7802	Intermediate Similarity	NPC476415
0.7802	Intermediate Similarity	NPC472976
0.7802	Intermediate Similarity	NPC299100
0.7802	Intermediate Similarity	NPC472977
0.7802	Intermediate Similarity	NPC103527
0.7791	Intermediate Similarity	NPC144258
0.7791	Intermediate Similarity	NPC472865
0.7791	Intermediate Similarity	NPC96095
0.7791	Intermediate Similarity	NPC164577
0.7778	Intermediate Similarity	NPC39362
0.7778	Intermediate Similarity	NPC472975
0.7778	Intermediate Similarity	NPC172101
0.7778	Intermediate Similarity	NPC73457
0.7778	Intermediate Similarity	NPC475806
0.7778	Intermediate Similarity	NPC114236
0.7765	Intermediate Similarity	NPC103486
0.7765	Intermediate Similarity	NPC279186
0.7765	Intermediate Similarity	NPC133391
0.7753	Intermediate Similarity	NPC119416
0.7753	Intermediate Similarity	NPC473999
0.7753	Intermediate Similarity	NPC5509
0.7753	Intermediate Similarity	NPC309603
0.7753	Intermediate Similarity	NPC473100
0.7753	Intermediate Similarity	NPC262043
0.775	Intermediate Similarity	NPC35656
0.775	Intermediate Similarity	NPC180015
0.775	Intermediate Similarity	NPC130016
0.775	Intermediate Similarity	NPC109576
0.775	Intermediate Similarity	NPC56747
0.7742	Intermediate Similarity	NPC472690
0.7742	Intermediate Similarity	NPC472689
0.7742	Intermediate Similarity	NPC477267
0.7742	Intermediate Similarity	NPC477268
0.7738	Intermediate Similarity	NPC37038
0.7738	Intermediate Similarity	NPC306095
0.7727	Intermediate Similarity	NPC231599
0.7722	Intermediate Similarity	NPC163020
0.7717	Intermediate Similarity	NPC53565
0.7717	Intermediate Similarity	NPC183012
0.7717	Intermediate Similarity	NPC180950
0.7717	Intermediate Similarity	NPC259286
0.7711	Intermediate Similarity	NPC297996
0.7711	Intermediate Similarity	NPC178852
0.7711	Intermediate Similarity	NPC30321
0.7711	Intermediate Similarity	NPC475994
0.7701	Intermediate Similarity	NPC52628
0.7701	Intermediate Similarity	NPC132228
0.7701	Intermediate Similarity	NPC241512
0.7701	Intermediate Similarity	NPC6185
0.7701	Intermediate Similarity	NPC8518
0.7701	Intermediate Similarity	NPC79573
0.7701	Intermediate Similarity	NPC470574
0.7701	Intermediate Similarity	NPC263997
0.7692	Intermediate Similarity	NPC472871
0.7692	Intermediate Similarity	NPC69454
0.7692	Intermediate Similarity	NPC472930
0.7692	Intermediate Similarity	NPC474807
0.7692	Intermediate Similarity	NPC475255
0.7692	Intermediate Similarity	NPC118490
0.7692	Intermediate Similarity	NPC131840
0.7684	Intermediate Similarity	NPC472637
0.7684	Intermediate Similarity	NPC115862
0.7683	Intermediate Similarity	NPC92080
0.7683	Intermediate Similarity	NPC250621
0.7674	Intermediate Similarity	NPC477373
0.7674	Intermediate Similarity	NPC105803
0.7674	Intermediate Similarity	NPC53733
0.7667	Intermediate Similarity	NPC476369
0.7667	Intermediate Similarity	NPC320026
0.7667	Intermediate Similarity	NPC476437

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 NPC226068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1653
0.2-0.3	3896
0.3-0.4	2344
0.4-0.5	658
0.5-0.6	221
0.6-0.7	156
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4623	Approved
0.8023	Intermediate Similarity	NPD3618	Phase 1
0.8023	Intermediate Similarity	NPD4519	Discontinued
0.7976	Intermediate Similarity	NPD4223	Phase 3
0.7976	Intermediate Similarity	NPD4221	Approved
0.7952	Intermediate Similarity	NPD4695	Discontinued
0.7791	Intermediate Similarity	NPD4197	Approved
0.7778	Intermediate Similarity	NPD5284	Approved
0.7778	Intermediate Similarity	NPD5281	Approved
0.7701	Intermediate Similarity	NPD5329	Approved
0.7692	Intermediate Similarity	NPD4202	Approved
0.7614	Intermediate Similarity	NPD4690	Approved
0.7614	Intermediate Similarity	NPD5690	Phase 2
0.7614	Intermediate Similarity	NPD5280	Approved
0.7614	Intermediate Similarity	NPD5205	Approved
0.7614	Intermediate Similarity	NPD4694	Approved
0.7614	Intermediate Similarity	NPD4688	Approved
0.7614	Intermediate Similarity	NPD4138	Approved
0.7614	Intermediate Similarity	NPD4689	Approved
0.7614	Intermediate Similarity	NPD4693	Phase 3
0.7586	Intermediate Similarity	NPD3133	Approved
0.7586	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD3665	Phase 1
0.7582	Intermediate Similarity	NPD7515	Phase 2
0.7556	Intermediate Similarity	NPD5328	Approved
0.7556	Intermediate Similarity	NPD4753	Phase 2
0.7553	Intermediate Similarity	NPD4755	Approved
0.7553	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD3617	Approved
0.7447	Intermediate Similarity	NPD4697	Phase 3
0.7423	Intermediate Similarity	NPD5211	Phase 2
0.7419	Intermediate Similarity	NPD7748	Approved
0.7396	Intermediate Similarity	NPD5286	Approved
0.7396	Intermediate Similarity	NPD4700	Approved
0.7396	Intermediate Similarity	NPD4696	Approved
0.7396	Intermediate Similarity	NPD5285	Approved
0.7391	Intermediate Similarity	NPD6079	Approved
0.7356	Intermediate Similarity	NPD3667	Approved
0.734	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD4629	Approved
0.7333	Intermediate Similarity	NPD3573	Approved
0.732	Intermediate Similarity	NPD5223	Approved
0.7303	Intermediate Similarity	NPD1694	Approved
0.7273	Intermediate Similarity	NPD5141	Approved
0.7263	Intermediate Similarity	NPD5222	Approved
0.7263	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5221	Approved
0.7245	Intermediate Similarity	NPD5225	Approved
0.7245	Intermediate Similarity	NPD4633	Approved
0.7245	Intermediate Similarity	NPD5226	Approved
0.7245	Intermediate Similarity	NPD5224	Approved
0.7234	Intermediate Similarity	NPD7900	Approved
0.7234	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5279	Phase 3
0.7215	Intermediate Similarity	NPD7331	Phase 2
0.7209	Intermediate Similarity	NPD4195	Approved
0.7191	Intermediate Similarity	NPD4786	Approved
0.7188	Intermediate Similarity	NPD5173	Approved
0.7174	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5174	Approved
0.7172	Intermediate Similarity	NPD4754	Approved
0.7172	Intermediate Similarity	NPD5175	Approved
0.716	Intermediate Similarity	NPD4137	Phase 3
0.7158	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD6399	Phase 3
0.7113	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD4096	Approved
0.7089	Intermediate Similarity	NPD7341	Phase 2
0.7073	Intermediate Similarity	NPD4691	Approved
0.7073	Intermediate Similarity	NPD4747	Approved
0.7053	Intermediate Similarity	NPD6001	Approved
0.7045	Intermediate Similarity	NPD4692	Approved
0.7045	Intermediate Similarity	NPD4139	Approved
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD4767	Approved
0.703	Intermediate Similarity	NPD4768	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.7021	Intermediate Similarity	NPD5693	Phase 1
0.701	Intermediate Similarity	NPD6083	Phase 2
0.701	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD3668	Phase 3
0.699	Remote Similarity	NPD6372	Approved
0.699	Remote Similarity	NPD6373	Approved
0.6989	Remote Similarity	NPD6080	Approved
0.6989	Remote Similarity	NPD6904	Approved
0.6989	Remote Similarity	NPD6673	Approved
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5697	Approved
0.6961	Remote Similarity	NPD5701	Approved
0.6947	Remote Similarity	NPD5133	Approved
0.6923	Remote Similarity	NPD1696	Phase 3
0.6915	Remote Similarity	NPD5207	Approved
0.6915	Remote Similarity	NPD5692	Phase 3
0.69	Remote Similarity	NPD5091	Approved
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6893	Remote Similarity	NPD5128	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD4730	Approved
0.6893	Remote Similarity	NPD6011	Approved
0.6893	Remote Similarity	NPD4729	Approved
0.6882	Remote Similarity	NPD5208	Approved
0.6882	Remote Similarity	NPD6672	Approved
0.6882	Remote Similarity	NPD5737	Approved
0.6882	Remote Similarity	NPD4518	Approved
0.6857	Remote Similarity	NPD6649	Approved
0.6857	Remote Similarity	NPD6650	Approved
0.6848	Remote Similarity	NPD7334	Approved
0.6848	Remote Similarity	NPD5330	Approved
0.6848	Remote Similarity	NPD6684	Approved
0.6848	Remote Similarity	NPD7146	Approved
0.6848	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD6409	Approved
0.6842	Remote Similarity	NPD5694	Approved
0.6842	Remote Similarity	NPD6050	Approved
0.6827	Remote Similarity	NPD6012	Approved
0.6827	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD6014	Approved
0.6824	Remote Similarity	NPD4058	Approved
0.6824	Remote Similarity	NPD4687	Approved
0.6824	Remote Similarity	NPD5733	Approved
0.6786	Remote Similarity	NPD5276	Approved
0.6768	Remote Similarity	NPD7638	Approved
0.6762	Remote Similarity	NPD5250	Approved
0.6762	Remote Similarity	NPD5169	Approved
0.6762	Remote Similarity	NPD5248	Approved
0.6762	Remote Similarity	NPD4634	Approved
0.6762	Remote Similarity	NPD5251	Approved
0.6762	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6762	Remote Similarity	NPD5249	Phase 3
0.6762	Remote Similarity	NPD5135	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD5247	Approved
0.6753	Remote Similarity	NPD287	Approved
0.6742	Remote Similarity	NPD7525	Registered
0.6735	Remote Similarity	NPD7614	Phase 1
0.6703	Remote Similarity	NPD4788	Approved
0.6702	Remote Similarity	NPD6903	Approved
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD7639	Approved
0.6699	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD5215	Approved
0.6698	Remote Similarity	NPD5217	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5216	Approved
0.6698	Remote Similarity	NPD8130	Phase 1
0.6698	Remote Similarity	NPD5127	Approved
0.6697	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6098	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6627	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4225	Approved
0.6588	Remote Similarity	NPD4243	Approved
0.6574	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD5168	Approved
0.6556	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6404	Discontinued
0.6531	Remote Similarity	NPD5282	Discontinued
0.6514	Remote Similarity	NPD5167	Approved
0.6509	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.65	Remote Similarity	NPD368	Approved
0.6495	Remote Similarity	NPD8035	Phase 2
0.6495	Remote Similarity	NPD8034	Phase 2
0.6476	Remote Similarity	NPD6412	Phase 2
0.6465	Remote Similarity	NPD5654	Approved
0.6455	Remote Similarity	NPD6274	Approved
0.6444	Remote Similarity	NPD7645	Phase 2
0.6437	Remote Similarity	NPD4784	Approved
0.6437	Remote Similarity	NPD4785	Approved
0.642	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6009	Approved
0.6396	Remote Similarity	NPD6317	Approved
0.6383	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4190	Phase 3
0.6364	Remote Similarity	NPD5275	Approved
0.6346	Remote Similarity	NPD6052	Approved
0.6339	Remote Similarity	NPD6335	Approved
0.6339	Remote Similarity	NPD6314	Approved
0.6339	Remote Similarity	NPD6313	Approved
0.6337	Remote Similarity	NPD5959	Approved
0.6333	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6411	Approved
0.6321	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.63	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7101	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