NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.11
Volume:	217.457
LogP:	0.359
LogD:	-1.417
LogS:	-0.83
# Rotatable Bonds:	0
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	3.993
Fsp3:	0.75
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:	-4.641
MDCK Permeability:	3.250595182180405e-05
Pgp-inhibitor:	0.191
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.413
Plasma Protein Binding (PPB):	39.44283676147461%
Volume Distribution (VD):	0.404
Pgp-substrate:	74.04188537597656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.504
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.378
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.488
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	15.009
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.094
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.057
Carcinogencity:	0.052
Eye Corrosion:	0.748
Eye Irritation:	0.351
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC38796

Natural Product ID:	NPC38796
*Common Name:**	Narchinol C
IUPAC Name:	(4R,4aS,5R,7R)-4,7-dihydroxy-4a,5-dimethyl-4,5,6,7-tetrahydronaphthalen-1-one
Synonyms:	Narchinol C
Standard InCHIKey:	MPVZRKBKGSHLGP-VNOQCFOKSA-N
Standard InCHI:	InChI=1S/C12H16O3/c1-7-5-8(13)6-9-10(14)3-4-11(15)12(7,9)2/h3-4,6-8,11,13,15H,5H2,1-2H3/t7-,8-,11-,12+/m1/s1
SMILES:	C[C@@H]1C[C@H](C=C2C(=O)C=C[C@H]([C@@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1933708
PubChem CID:	56835096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	21600.0	nM	PMID[458608]

☑ 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 NPC38796 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	181
0.1-0.2	1114
0.2-0.3	5151
0.3-0.4	12648
0.4-0.5	12540
0.5-0.6	6988
0.6-0.7	3573
0.7-0.8	450
0.8-0.85	37
0.85-0.9	11
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC158411
0.9605	High Similarity	NPC19900
0.8974	High Similarity	NPC475994
0.8816	High Similarity	NPC186042
0.8718	High Similarity	NPC470525
0.8625	High Similarity	NPC308038
0.8608	High Similarity	NPC471061
0.8571	High Similarity	NPC472974
0.85	High Similarity	NPC62336
0.8481	Intermediate Similarity	NPC263582
0.8462	Intermediate Similarity	NPC215050
0.8452	Intermediate Similarity	NPC15807
0.8452	Intermediate Similarity	NPC476426
0.8375	Intermediate Similarity	NPC74995
0.8353	Intermediate Similarity	NPC472985
0.8353	Intermediate Similarity	NPC194417
0.8353	Intermediate Similarity	NPC472986
0.8333	Intermediate Similarity	NPC201562
0.8333	Intermediate Similarity	NPC323437
0.8333	Intermediate Similarity	NPC29542
0.8313	Intermediate Similarity	NPC93590
0.8295	Intermediate Similarity	NPC116726
0.8293	Intermediate Similarity	NPC172013
0.8293	Intermediate Similarity	NPC271104
0.8289	Intermediate Similarity	NPC117804
0.8222	Intermediate Similarity	NPC476245
0.8193	Intermediate Similarity	NPC6663
0.8171	Intermediate Similarity	NPC152061
0.8171	Intermediate Similarity	NPC281138
0.8125	Intermediate Similarity	NPC114236
0.8118	Intermediate Similarity	NPC476412
0.8111	Intermediate Similarity	NPC196227
0.8095	Intermediate Similarity	NPC279186
0.8072	Intermediate Similarity	NPC45495
0.8072	Intermediate Similarity	NPC148685
0.8072	Intermediate Similarity	NPC157895
0.8072	Intermediate Similarity	NPC104120
0.8068	Intermediate Similarity	NPC473100
0.8068	Intermediate Similarity	NPC123912
0.8046	Intermediate Similarity	NPC287079
0.8043	Intermediate Similarity	NPC135685
0.8043	Intermediate Similarity	NPC470522
0.8023	Intermediate Similarity	NPC179006
0.8023	Intermediate Similarity	NPC474853
0.8	Intermediate Similarity	NPC474736
0.8	Intermediate Similarity	NPC105173
0.7978	Intermediate Similarity	NPC473099
0.7976	Intermediate Similarity	NPC116797
0.7976	Intermediate Similarity	NPC470298
0.7975	Intermediate Similarity	NPC95863
0.7957	Intermediate Similarity	NPC103051
0.7952	Intermediate Similarity	NPC7232
0.7949	Intermediate Similarity	NPC136473
0.7935	Intermediate Similarity	NPC117133
0.7931	Intermediate Similarity	NPC222613
0.7931	Intermediate Similarity	NPC118648
0.7931	Intermediate Similarity	NPC475022
0.7931	Intermediate Similarity	NPC94666
0.7927	Intermediate Similarity	NPC203403
0.7927	Intermediate Similarity	NPC197659
0.7927	Intermediate Similarity	NPC97377
0.7922	Intermediate Similarity	NPC106613
0.7922	Intermediate Similarity	NPC269985
0.7907	Intermediate Similarity	NPC7927
0.7907	Intermediate Similarity	NPC472326
0.7907	Intermediate Similarity	NPC230527
0.7889	Intermediate Similarity	NPC233116
0.7882	Intermediate Similarity	NPC103486
0.7865	Intermediate Similarity	NPC472983
0.7865	Intermediate Similarity	NPC474918
0.7865	Intermediate Similarity	NPC472973
0.7857	Intermediate Similarity	NPC471514
0.7857	Intermediate Similarity	NPC2482
0.7841	Intermediate Similarity	NPC470523
0.7841	Intermediate Similarity	NPC136548
0.7831	Intermediate Similarity	NPC275494
0.7831	Intermediate Similarity	NPC231739
0.7831	Intermediate Similarity	NPC471409
0.7826	Intermediate Similarity	NPC271195
0.7816	Intermediate Similarity	NPC474083
0.7805	Intermediate Similarity	NPC7629
0.7805	Intermediate Similarity	NPC151622
0.7802	Intermediate Similarity	NPC134826
0.7802	Intermediate Similarity	NPC109305
0.7791	Intermediate Similarity	NPC49019
0.7791	Intermediate Similarity	NPC251475
0.7791	Intermediate Similarity	NPC169941
0.7778	Intermediate Similarity	NPC48010
0.7778	Intermediate Similarity	NPC134321
0.7766	Intermediate Similarity	NPC23364
0.7766	Intermediate Similarity	NPC478056
0.7765	Intermediate Similarity	NPC14151
0.7765	Intermediate Similarity	NPC136150
0.7765	Intermediate Similarity	NPC121984
0.7753	Intermediate Similarity	NPC249889
0.7753	Intermediate Similarity	NPC470524
0.7753	Intermediate Similarity	NPC471791
0.7753	Intermediate Similarity	NPC471793
0.7753	Intermediate Similarity	NPC193843
0.7738	Intermediate Similarity	NPC472490
0.7727	Intermediate Similarity	NPC82979
0.7727	Intermediate Similarity	NPC470955
0.7722	Intermediate Similarity	NPC250928
0.7722	Intermediate Similarity	NPC10758
0.7717	Intermediate Similarity	NPC472976
0.7717	Intermediate Similarity	NPC472977
0.7717	Intermediate Similarity	NPC78159
0.7711	Intermediate Similarity	NPC257666
0.7711	Intermediate Similarity	NPC266193
0.7711	Intermediate Similarity	NPC34110
0.7708	Intermediate Similarity	NPC293753
0.7701	Intermediate Similarity	NPC473246
0.7701	Intermediate Similarity	NPC470812
0.7701	Intermediate Similarity	NPC40687
0.7692	Intermediate Similarity	NPC73457
0.7692	Intermediate Similarity	NPC475806
0.7692	Intermediate Similarity	NPC131872
0.7692	Intermediate Similarity	NPC472978
0.7674	Intermediate Similarity	NPC212083
0.7674	Intermediate Similarity	NPC92226
0.7667	Intermediate Similarity	NPC214387
0.7667	Intermediate Similarity	NPC309603
0.7667	Intermediate Similarity	NPC119416
0.7667	Intermediate Similarity	NPC473999
0.7667	Intermediate Similarity	NPC310236
0.7667	Intermediate Similarity	NPC186688
0.766	Intermediate Similarity	NPC320306
0.7654	Intermediate Similarity	NPC153660
0.7654	Intermediate Similarity	NPC247586
0.7654	Intermediate Similarity	NPC275098
0.7647	Intermediate Similarity	NPC472301
0.7647	Intermediate Similarity	NPC108955
0.7647	Intermediate Similarity	NPC472478
0.764	Intermediate Similarity	NPC58063
0.764	Intermediate Similarity	NPC220930
0.764	Intermediate Similarity	NPC312561
0.764	Intermediate Similarity	NPC272039
0.764	Intermediate Similarity	NPC298904
0.7634	Intermediate Similarity	NPC472932
0.7634	Intermediate Similarity	NPC259286
0.7634	Intermediate Similarity	NPC272617
0.7629	Intermediate Similarity	NPC247957
0.7629	Intermediate Similarity	NPC249187
0.7629	Intermediate Similarity	NPC111323
0.7619	Intermediate Similarity	NPC297996
0.7619	Intermediate Similarity	NPC189485
0.7619	Intermediate Similarity	NPC74410
0.7619	Intermediate Similarity	NPC178852
0.7614	Intermediate Similarity	NPC471224
0.7614	Intermediate Similarity	NPC32037
0.7614	Intermediate Similarity	NPC274724
0.7614	Intermediate Similarity	NPC52628
0.7614	Intermediate Similarity	NPC70685
0.7614	Intermediate Similarity	NPC255174
0.7609	Intermediate Similarity	NPC69454
0.7609	Intermediate Similarity	NPC472930
0.7604	Intermediate Similarity	NPC470184
0.7604	Intermediate Similarity	NPC115862
0.7604	Intermediate Similarity	NPC472924
0.759	Intermediate Similarity	NPC469646
0.759	Intermediate Similarity	NPC472305
0.759	Intermediate Similarity	NPC250621
0.7586	Intermediate Similarity	NPC64600
0.7586	Intermediate Similarity	NPC297398
0.7586	Intermediate Similarity	NPC110150
0.7586	Intermediate Similarity	NPC66764
0.7582	Intermediate Similarity	NPC69622
0.7582	Intermediate Similarity	NPC230332
0.7582	Intermediate Similarity	NPC158488
0.7582	Intermediate Similarity	NPC128672
0.7582	Intermediate Similarity	NPC232202
0.7582	Intermediate Similarity	NPC477147
0.7582	Intermediate Similarity	NPC477149
0.7579	Intermediate Similarity	NPC197386
0.7579	Intermediate Similarity	NPC235464
0.7579	Intermediate Similarity	NPC166745
0.7561	Intermediate Similarity	NPC213223
0.7558	Intermediate Similarity	NPC226068
0.7558	Intermediate Similarity	NPC225515
0.7558	Intermediate Similarity	NPC55869
0.7556	Intermediate Similarity	NPC104560
0.7556	Intermediate Similarity	NPC471722
0.7556	Intermediate Similarity	NPC53454
0.7556	Intermediate Similarity	NPC473229
0.7556	Intermediate Similarity	NPC158778
0.7556	Intermediate Similarity	NPC476796
0.7556	Intermediate Similarity	NPC474854
0.7553	Intermediate Similarity	NPC456
0.7553	Intermediate Similarity	NPC249954
0.7553	Intermediate Similarity	NPC202833
0.7553	Intermediate Similarity	NPC472941
0.7531	Intermediate Similarity	NPC84790
0.7529	Intermediate Similarity	NPC476177
0.7529	Intermediate Similarity	NPC474113
0.7528	Intermediate Similarity	NPC145879
0.7528	Intermediate Similarity	NPC474733
0.7528	Intermediate Similarity	NPC31564
0.7528	Intermediate Similarity	NPC473226
0.7528	Intermediate Similarity	NPC474778
0.7528	Intermediate Similarity	NPC198761

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 NPC38796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1630
0.2-0.3	3873
0.3-0.4	2369
0.4-0.5	714
0.5-0.6	288
0.6-0.7	98
0.7-0.8	8
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
0.7528	Intermediate Similarity	NPD3618	Phase 1
0.7528	Intermediate Similarity	NPD5279	Phase 3
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.7471	Intermediate Similarity	NPD3667	Approved
0.7442	Intermediate Similarity	NPD4695	Discontinued
0.7333	Intermediate Similarity	NPD4519	Discontinued
0.7333	Intermediate Similarity	NPD4623	Approved
0.7312	Intermediate Similarity	NPD6079	Approved
0.7303	Intermediate Similarity	NPD4786	Approved
0.7262	Intermediate Similarity	NPD8264	Approved
0.7241	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5778	Approved
0.7234	Intermediate Similarity	NPD5779	Approved
0.7222	Intermediate Similarity	NPD5363	Approved
0.7222	Intermediate Similarity	NPD1696	Phase 3
0.7204	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD5690	Phase 2
0.7097	Intermediate Similarity	NPD5328	Approved
0.7083	Intermediate Similarity	NPD5210	Approved
0.7083	Intermediate Similarity	NPD4629	Approved
0.7033	Intermediate Similarity	NPD1694	Approved
0.7011	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5221	Approved
0.701	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5211	Phase 2
0.6947	Remote Similarity	NPD7515	Phase 2
0.6939	Remote Similarity	NPD5173	Approved
0.6915	Remote Similarity	NPD4753	Phase 2
0.6889	Remote Similarity	NPD4270	Approved
0.6889	Remote Similarity	NPD4269	Approved
0.6889	Remote Similarity	NPD4221	Approved
0.6889	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD4202	Approved
0.6863	Remote Similarity	NPD5141	Approved
0.6854	Remote Similarity	NPD4252	Approved
0.6837	Remote Similarity	NPD4697	Phase 3
0.6813	Remote Similarity	NPD6110	Phase 1
0.6809	Remote Similarity	NPD4518	Approved
0.6804	Remote Similarity	NPD5282	Discontinued
0.68	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD4696	Approved
0.68	Remote Similarity	NPD5286	Approved
0.6774	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5280	Approved
0.6774	Remote Similarity	NPD4694	Approved
0.6771	Remote Similarity	NPD6411	Approved
0.6771	Remote Similarity	NPD5281	Approved
0.6771	Remote Similarity	NPD5284	Approved
0.6739	Remote Similarity	NPD4197	Approved
0.6739	Remote Similarity	NPD3668	Phase 3
0.6735	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5223	Approved
0.6707	Remote Similarity	NPD7331	Phase 2
0.6703	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6399	Phase 3
0.67	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6636	Remote Similarity	NPD7115	Discovery
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6633	Remote Similarity	NPD7748	Approved
0.663	Remote Similarity	NPD5362	Discontinued
0.6629	Remote Similarity	NPD7145	Approved
0.6629	Remote Similarity	NPD3617	Approved
0.6602	Remote Similarity	NPD5175	Approved
0.6602	Remote Similarity	NPD5174	Approved
0.66	Remote Similarity	NPD7902	Approved
0.66	Remote Similarity	NPD4755	Approved
0.6598	Remote Similarity	NPD7637	Suspended
0.6596	Remote Similarity	NPD7334	Approved
0.6596	Remote Similarity	NPD4690	Approved
0.6596	Remote Similarity	NPD4689	Approved
0.6596	Remote Similarity	NPD7521	Approved
0.6596	Remote Similarity	NPD5330	Approved
0.6596	Remote Similarity	NPD4688	Approved
0.6596	Remote Similarity	NPD4138	Approved
0.6596	Remote Similarity	NPD6409	Approved
0.6596	Remote Similarity	NPD5205	Approved
0.6596	Remote Similarity	NPD7146	Approved
0.6596	Remote Similarity	NPD4693	Phase 3
0.6596	Remote Similarity	NPD6684	Approved
0.6596	Remote Similarity	NPD5786	Approved
0.6593	Remote Similarity	NPD6902	Approved
0.6588	Remote Similarity	NPD4691	Approved
0.6566	Remote Similarity	NPD5695	Phase 3
0.6562	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4195	Approved
0.6556	Remote Similarity	NPD6929	Approved
0.6552	Remote Similarity	NPD4058	Approved
0.6552	Remote Similarity	NPD4687	Approved
0.6543	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4634	Approved
0.6535	Remote Similarity	NPD7638	Approved
0.6526	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6925	Approved
0.6517	Remote Similarity	NPD5776	Phase 2
0.6517	Remote Similarity	NPD4756	Discovery
0.6512	Remote Similarity	NPD5276	Approved
0.6509	Remote Similarity	NPD6686	Approved
0.6495	Remote Similarity	NPD46	Approved
0.6495	Remote Similarity	NPD6698	Approved
0.6495	Remote Similarity	NPD4096	Approved
0.6484	Remote Similarity	NPD6931	Approved
0.6484	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD4137	Phase 3
0.6471	Remote Similarity	NPD4700	Approved
0.6458	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7154	Phase 3
0.6452	Remote Similarity	NPD4788	Approved
0.6444	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4268	Approved
0.6444	Remote Similarity	NPD4271	Approved
0.6436	Remote Similarity	NPD6084	Phase 2
0.6436	Remote Similarity	NPD6083	Phase 2
0.642	Remote Similarity	NPD368	Approved
0.6415	Remote Similarity	NPD5697	Approved
0.6415	Remote Similarity	NPD6412	Phase 2
0.6413	Remote Similarity	NPD5369	Approved
0.6404	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4747	Approved
0.6389	Remote Similarity	NPD6371	Approved
0.6386	Remote Similarity	NPD7341	Phase 2
0.6373	Remote Similarity	NPD5696	Approved
0.6373	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD5733	Approved
0.6355	Remote Similarity	NPD4730	Approved
0.6355	Remote Similarity	NPD6881	Approved
0.6355	Remote Similarity	NPD6011	Approved
0.6355	Remote Similarity	NPD5168	Approved
0.6355	Remote Similarity	NPD6899	Approved
0.6355	Remote Similarity	NPD4729	Approved
0.6354	Remote Similarity	NPD3573	Approved
0.6333	Remote Similarity	NPD6932	Approved
0.633	Remote Similarity	NPD6649	Approved
0.633	Remote Similarity	NPD6650	Approved
0.6327	Remote Similarity	NPD5207	Approved
0.6311	Remote Similarity	NPD6404	Discontinued
0.631	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3704	Approved
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD4821	Approved
0.6304	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD4820	Approved
0.63	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD6014	Approved
0.6296	Remote Similarity	NPD6013	Approved
0.6296	Remote Similarity	NPD6012	Approved
0.6292	Remote Similarity	NPD7339	Approved
0.6292	Remote Similarity	NPD8039	Approved
0.6292	Remote Similarity	NPD6942	Approved
0.6289	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD5737	Approved
0.6286	Remote Similarity	NPD4754	Approved
0.6282	Remote Similarity	NPD342	Phase 1
0.6277	Remote Similarity	NPD6695	Phase 3
0.6277	Remote Similarity	NPD5331	Approved
0.6277	Remote Similarity	NPD5332	Approved
0.6263	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD287	Approved
0.625	Remote Similarity	NPD4732	Discontinued
0.625	Remote Similarity	NPD4249	Approved
0.6239	Remote Similarity	NPD5169	Approved
0.6239	Remote Similarity	NPD5250	Approved
0.6239	Remote Similarity	NPD5249	Phase 3
0.6239	Remote Similarity	NPD7290	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD5247	Approved
0.6239	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5248	Approved
0.6239	Remote Similarity	NPD5135	Approved
0.6237	Remote Similarity	NPD6898	Phase 1
0.6237	Remote Similarity	NPD4139	Approved
0.6237	Remote Similarity	NPD4692	Approved
0.6237	Remote Similarity	NPD4790	Discontinued
0.6211	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7143	Approved
0.6207	Remote Similarity	NPD7144	Approved
0.6204	Remote Similarity	NPD5128	Approved
0.62	Remote Similarity	NPD5133	Approved
0.6195	Remote Similarity	NPD6009	Approved
0.619	Remote Similarity	NPD5091	Approved
0.6186	Remote Similarity	NPD4251	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