NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.16
Volume:	254.685
LogP:	1.099
LogD:	1.3
LogS:	-0.949
# 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:	0.683
Synthetic Accessibility Score:	4.428
Fsp3:	0.786
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:	-4.538
MDCK Permeability:	1.3581998246081639e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.223

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	14.375720977783203%
Volume Distribution (VD):	1.201
Pgp-substrate:	67.2975845336914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.705
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	15.163
Half-life (T1/2):	0.679

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.404
Carcinogencity:	0.94
Eye Corrosion:	0.727
Eye Irritation:	0.613
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC104120

Natural Product ID:	NPC104120
*Common Name:**	Laevinol B
IUPAC Name:	1-[(1R,2S,6S,8S,8aS)-2,6-dihydroxy-8,8a-dimethyl-2,3,4,6,7,8-hexahydro-1H-naphthalen-1-yl]ethanone
Synonyms:	laevinol B
Standard InCHIKey:	UCBOCFFXBGGPKI-XPBAASLYSA-N
Standard InCHI:	InChI=1S/C14H22O3/c1-8-6-11(16)7-10-4-5-12(17)13(9(2)15)14(8,10)3/h7-8,11-13,16-17H,4-6H2,1-3H3/t8-,11-,12-,13-,14+/m0/s1
SMILES:	C[C@H]1C[C@@H](C=C2CC[C@@H]([C@H](C(=O)C)[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463570
PubChem CID:	5326375
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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
NPO6460	Lemnalia laevis	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16378367]
NPO6460	Lemnalia laevis	Species	Nephtheidae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[521562]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[521562]

☑ 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 NPC104120 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	163
0.1-0.2	1086
0.2-0.3	4784
0.3-0.4	12148
0.4-0.5	12163
0.5-0.6	6763
0.6-0.7	4201
0.7-0.8	1278
0.8-0.85	85
0.85-0.9	16
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148685
1.0	High Similarity	NPC157895
0.9342	High Similarity	NPC308038
0.9333	High Similarity	NPC74995
0.925	High Similarity	NPC198761
0.9091	High Similarity	NPC152061
0.9012	High Similarity	NPC470955
0.8987	High Similarity	NPC93590
0.8974	High Similarity	NPC172013
0.8947	High Similarity	NPC263582
0.8916	High Similarity	NPC472970
0.8916	High Similarity	NPC472971
0.8875	High Similarity	NPC105173
0.8846	High Similarity	NPC281138
0.8831	High Similarity	NPC197659
0.878	High Similarity	NPC194417
0.878	High Similarity	NPC472985
0.878	High Similarity	NPC472986
0.8718	High Similarity	NPC62336
0.8659	High Similarity	NPC52628
0.8625	High Similarity	NPC14151
0.8608	High Similarity	NPC7232
0.8588	High Similarity	NPC230332
0.8554	High Similarity	NPC82979
0.8554	High Similarity	NPC473226
0.8554	High Similarity	NPC472974
0.8519	High Similarity	NPC48362
0.85	High Similarity	NPC45495
0.8481	Intermediate Similarity	NPC297996
0.8481	Intermediate Similarity	NPC178852
0.8481	Intermediate Similarity	NPC475994
0.8471	Intermediate Similarity	NPC472983
0.8471	Intermediate Similarity	NPC472973
0.8452	Intermediate Similarity	NPC298904
0.8434	Intermediate Similarity	NPC179006
0.8434	Intermediate Similarity	NPC274724
0.8434	Intermediate Similarity	NPC474083
0.8434	Intermediate Similarity	NPC474853
0.8434	Intermediate Similarity	NPC471224
0.8415	Intermediate Similarity	NPC64600
0.8415	Intermediate Similarity	NPC169941
0.8415	Intermediate Similarity	NPC251475
0.8395	Intermediate Similarity	NPC473420
0.8372	Intermediate Similarity	NPC134321
0.8354	Intermediate Similarity	NPC203403
0.8354	Intermediate Similarity	NPC34110
0.8354	Intermediate Similarity	NPC257666
0.8354	Intermediate Similarity	NPC266193
0.8353	Intermediate Similarity	NPC471791
0.8353	Intermediate Similarity	NPC471793
0.8333	Intermediate Similarity	NPC114236
0.8333	Intermediate Similarity	NPC476043
0.8333	Intermediate Similarity	NPC322159
0.8313	Intermediate Similarity	NPC40687
0.8313	Intermediate Similarity	NPC227132
0.8313	Intermediate Similarity	NPC476412
0.8312	Intermediate Similarity	NPC247586
0.8312	Intermediate Similarity	NPC186042
0.8276	Intermediate Similarity	NPC472978
0.8276	Intermediate Similarity	NPC116726
0.8272	Intermediate Similarity	NPC471514
0.8272	Intermediate Similarity	NPC306095
0.8272	Intermediate Similarity	NPC472301
0.8256	Intermediate Similarity	NPC69627
0.8256	Intermediate Similarity	NPC309603
0.8256	Intermediate Similarity	NPC473100
0.8256	Intermediate Similarity	NPC473999
0.825	Intermediate Similarity	NPC239098
0.8235	Intermediate Similarity	NPC272039
0.8235	Intermediate Similarity	NPC220930
0.8228	Intermediate Similarity	NPC470525
0.8228	Intermediate Similarity	NPC250621
0.8228	Intermediate Similarity	NPC472305
0.8214	Intermediate Similarity	NPC133954
0.8214	Intermediate Similarity	NPC15807
0.8214	Intermediate Similarity	NPC79573
0.8214	Intermediate Similarity	NPC70685
0.8214	Intermediate Similarity	NPC476426
0.8214	Intermediate Similarity	NPC470574
0.8182	Intermediate Similarity	NPC69454
0.8182	Intermediate Similarity	NPC477520
0.8171	Intermediate Similarity	NPC226068
0.8171	Intermediate Similarity	NPC116797
0.8161	Intermediate Similarity	NPC48010
0.8161	Intermediate Similarity	NPC128672
0.8161	Intermediate Similarity	NPC473099
0.8148	Intermediate Similarity	NPC19900
0.814	Intermediate Similarity	NPC104560
0.814	Intermediate Similarity	NPC471724
0.814	Intermediate Similarity	NPC474854
0.8125	Intermediate Similarity	NPC97377
0.8125	Intermediate Similarity	NPC325946
0.8118	Intermediate Similarity	NPC469994
0.8118	Intermediate Similarity	NPC213412
0.8118	Intermediate Similarity	NPC74363
0.8118	Intermediate Similarity	NPC475862
0.8095	Intermediate Similarity	NPC470812
0.8095	Intermediate Similarity	NPC165064
0.809	Intermediate Similarity	NPC196227
0.809	Intermediate Similarity	NPC472976
0.809	Intermediate Similarity	NPC472977
0.8077	Intermediate Similarity	NPC275098
0.8072	Intermediate Similarity	NPC151519
0.8072	Intermediate Similarity	NPC38796
0.8072	Intermediate Similarity	NPC212083
0.8072	Intermediate Similarity	NPC158411
0.8068	Intermediate Similarity	NPC73457
0.8068	Intermediate Similarity	NPC63748
0.8068	Intermediate Similarity	NPC475806
0.8068	Intermediate Similarity	NPC6255
0.8068	Intermediate Similarity	NPC233116
0.8068	Intermediate Similarity	NPC472975
0.8068	Intermediate Similarity	NPC473998
0.8068	Intermediate Similarity	NPC172101
0.8068	Intermediate Similarity	NPC471588
0.8052	Intermediate Similarity	NPC34834
0.8049	Intermediate Similarity	NPC233352
0.8049	Intermediate Similarity	NPC2482
0.8049	Intermediate Similarity	NPC824
0.8049	Intermediate Similarity	NPC138492
0.8049	Intermediate Similarity	NPC271104
0.8046	Intermediate Similarity	NPC2983
0.8046	Intermediate Similarity	NPC281524
0.8026	Intermediate Similarity	NPC96484
0.8025	Intermediate Similarity	NPC275494
0.8025	Intermediate Similarity	NPC207772
0.8025	Intermediate Similarity	NPC471409
0.8023	Intermediate Similarity	NPC73064
0.8	Intermediate Similarity	NPC167873
0.8	Intermediate Similarity	NPC272617
0.8	Intermediate Similarity	NPC7629
0.8	Intermediate Similarity	NPC151622
0.8	Intermediate Similarity	NPC271195
0.8	Intermediate Similarity	NPC1973
0.8	Intermediate Similarity	NPC471344
0.8	Intermediate Similarity	NPC259286
0.8	Intermediate Similarity	NPC476245
0.8	Intermediate Similarity	NPC134067
0.7978	Intermediate Similarity	NPC115021
0.7978	Intermediate Similarity	NPC472930
0.7978	Intermediate Similarity	NPC109305
0.7976	Intermediate Similarity	NPC297398
0.7976	Intermediate Similarity	NPC470948
0.7975	Intermediate Similarity	NPC215050
0.7955	Intermediate Similarity	NPC232202
0.7955	Intermediate Similarity	NPC69622
0.7955	Intermediate Similarity	NPC86372
0.7955	Intermediate Similarity	NPC172361
0.7952	Intermediate Similarity	NPC121984
0.7952	Intermediate Similarity	NPC6663
0.7952	Intermediate Similarity	NPC3915
0.7949	Intermediate Similarity	NPC23954
0.7949	Intermediate Similarity	NPC477792
0.7935	Intermediate Similarity	NPC316598
0.7931	Intermediate Similarity	NPC158778
0.7931	Intermediate Similarity	NPC476796
0.7931	Intermediate Similarity	NPC471722
0.7931	Intermediate Similarity	NPC53454
0.7931	Intermediate Similarity	NPC328539
0.7931	Intermediate Similarity	NPC472802
0.7931	Intermediate Similarity	NPC53911
0.7931	Intermediate Similarity	NPC328313
0.7927	Intermediate Similarity	NPC229204
0.7927	Intermediate Similarity	NPC474113
0.7922	Intermediate Similarity	NPC474248
0.7912	Intermediate Similarity	NPC249954
0.7912	Intermediate Similarity	NPC117133
0.7912	Intermediate Similarity	NPC242848
0.7907	Intermediate Similarity	NPC94755
0.7907	Intermediate Similarity	NPC476104
0.7907	Intermediate Similarity	NPC158393
0.7907	Intermediate Similarity	NPC477579
0.7907	Intermediate Similarity	NPC179591
0.7907	Intermediate Similarity	NPC235341
0.7907	Intermediate Similarity	NPC73038
0.7907	Intermediate Similarity	NPC95594
0.7907	Intermediate Similarity	NPC6979
0.7907	Intermediate Similarity	NPC202394
0.7907	Intermediate Similarity	NPC325594
0.7907	Intermediate Similarity	NPC72133
0.7901	Intermediate Similarity	NPC91594
0.7889	Intermediate Similarity	NPC8993
0.7889	Intermediate Similarity	NPC474529
0.7889	Intermediate Similarity	NPC299100
0.7889	Intermediate Similarity	NPC469406
0.7889	Intermediate Similarity	NPC474690
0.7882	Intermediate Similarity	NPC161423
0.7882	Intermediate Similarity	NPC321187
0.7882	Intermediate Similarity	NPC227064
0.7882	Intermediate Similarity	NPC221758
0.7882	Intermediate Similarity	NPC85774
0.7882	Intermediate Similarity	NPC180834
0.7882	Intermediate Similarity	NPC59453
0.7882	Intermediate Similarity	NPC58841
0.7882	Intermediate Similarity	NPC329043
0.7882	Intermediate Similarity	NPC473246
0.7882	Intermediate Similarity	NPC82902
0.7882	Intermediate Similarity	NPC214043
0.7875	Intermediate Similarity	NPC476795
0.7865	Intermediate Similarity	NPC282616

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 NPC104120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1533
0.2-0.3	3800
0.3-0.4	2442
0.4-0.5	777
0.5-0.6	231
0.6-0.7	193
0.7-0.8	21
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
0.8118	Intermediate Similarity	NPD3618	Phase 1
0.8072	Intermediate Similarity	NPD3667	Approved
0.7882	Intermediate Similarity	NPD3665	Phase 1
0.7882	Intermediate Similarity	NPD4786	Approved
0.7882	Intermediate Similarity	NPD3666	Approved
0.7882	Intermediate Similarity	NPD3133	Approved
0.7841	Intermediate Similarity	NPD5328	Approved
0.7701	Intermediate Similarity	NPD5279	Phase 3
0.7667	Intermediate Similarity	NPD6079	Approved
0.7667	Intermediate Similarity	NPD7515	Phase 2
0.7582	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4519	Discontinued
0.7412	Intermediate Similarity	NPD4695	Discontinued
0.7391	Intermediate Similarity	NPD5778	Approved
0.7391	Intermediate Similarity	NPD5779	Approved
0.734	Intermediate Similarity	NPD5221	Approved
0.734	Intermediate Similarity	NPD5222	Approved
0.734	Intermediate Similarity	NPD4697	Phase 3
0.734	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5211	Phase 2
0.7312	Intermediate Similarity	NPD7748	Approved
0.7283	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD3668	Phase 3
0.7263	Intermediate Similarity	NPD4755	Approved
0.7263	Intermediate Similarity	NPD5173	Approved
0.7253	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD4221	Approved
0.7241	Intermediate Similarity	NPD4223	Phase 3
0.7229	Intermediate Similarity	NPD8264	Approved
0.7191	Intermediate Similarity	NPD1694	Approved
0.7188	Intermediate Similarity	NPD4225	Approved
0.7176	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5141	Approved
0.7113	Intermediate Similarity	NPD5285	Approved
0.7113	Intermediate Similarity	NPD5286	Approved
0.7113	Intermediate Similarity	NPD4700	Approved
0.7113	Intermediate Similarity	NPD4696	Approved
0.7093	Intermediate Similarity	NPD7645	Phase 2
0.7083	Intermediate Similarity	NPD7902	Approved
0.7079	Intermediate Similarity	NPD4197	Approved
0.7065	Intermediate Similarity	NPD6101	Approved
0.7065	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4269	Approved
0.7045	Intermediate Similarity	NPD4270	Approved
0.7041	Intermediate Similarity	NPD5223	Approved
0.7021	Intermediate Similarity	NPD6399	Phase 3
0.7013	Intermediate Similarity	NPD368	Approved
0.7	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD1696	Phase 3
0.6977	Remote Similarity	NPD3617	Approved
0.697	Remote Similarity	NPD5225	Approved
0.697	Remote Similarity	NPD5226	Approved
0.697	Remote Similarity	NPD4633	Approved
0.697	Remote Similarity	NPD5224	Approved
0.6941	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7640	Approved
0.6939	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD6409	Approved
0.6923	Remote Similarity	NPD4690	Approved
0.6923	Remote Similarity	NPD4688	Approved
0.6923	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD7334	Approved
0.6923	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD7521	Approved
0.6923	Remote Similarity	NPD6684	Approved
0.6923	Remote Similarity	NPD4694	Approved
0.6923	Remote Similarity	NPD7146	Approved
0.6923	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4689	Approved
0.6923	Remote Similarity	NPD4693	Phase 3
0.6923	Remote Similarity	NPD5280	Approved
0.6923	Remote Similarity	NPD5205	Approved
0.6916	Remote Similarity	NPD7115	Discovery
0.69	Remote Similarity	NPD4754	Approved
0.69	Remote Similarity	NPD5174	Approved
0.69	Remote Similarity	NPD5175	Approved
0.6875	Remote Similarity	NPD5210	Approved
0.6875	Remote Similarity	NPD4629	Approved
0.6854	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7638	Approved
0.6827	Remote Similarity	NPD4634	Approved
0.6824	Remote Similarity	NPD6942	Approved
0.6824	Remote Similarity	NPD7339	Approved
0.6818	Remote Similarity	NPD7525	Registered
0.6818	Remote Similarity	NPD4252	Approved
0.6818	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD5785	Approved
0.6778	Remote Similarity	NPD4788	Approved
0.6774	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6903	Approved
0.6771	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7900	Approved
0.6765	Remote Similarity	NPD6402	Approved
0.6765	Remote Similarity	NPD7128	Approved
0.6765	Remote Similarity	NPD4767	Approved
0.6765	Remote Similarity	NPD5739	Approved
0.6765	Remote Similarity	NPD6675	Approved
0.6765	Remote Similarity	NPD4768	Approved
0.6742	Remote Similarity	NPD4139	Approved
0.6742	Remote Similarity	NPD4692	Approved
0.6739	Remote Similarity	NPD5786	Approved
0.6737	Remote Similarity	NPD7637	Suspended
0.6735	Remote Similarity	NPD6083	Phase 2
0.6735	Remote Similarity	NPD6084	Phase 2
0.6706	Remote Similarity	NPD6926	Approved
0.6706	Remote Similarity	NPD6924	Approved
0.6705	Remote Similarity	NPD6929	Approved
0.6701	Remote Similarity	NPD5695	Phase 3
0.6699	Remote Similarity	NPD5701	Approved
0.6699	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD3573	Approved
0.6635	Remote Similarity	NPD5128	Approved
0.6635	Remote Similarity	NPD7320	Approved
0.6635	Remote Similarity	NPD6881	Approved
0.6635	Remote Similarity	NPD5168	Approved
0.6635	Remote Similarity	NPD6011	Approved
0.6635	Remote Similarity	NPD4729	Approved
0.6635	Remote Similarity	NPD4730	Approved
0.6635	Remote Similarity	NPD6899	Approved
0.6632	Remote Similarity	NPD4096	Approved
0.6629	Remote Similarity	NPD6931	Approved
0.6629	Remote Similarity	NPD6930	Phase 2
0.6627	Remote Similarity	NPD4137	Phase 3
0.6627	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5737	Approved
0.6596	Remote Similarity	NPD6672	Approved
0.6593	Remote Similarity	NPD5362	Discontinued
0.6591	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD6014	Approved
0.6571	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD6372	Approved
0.6571	Remote Similarity	NPD6013	Approved
0.6562	Remote Similarity	NPD5284	Approved
0.6562	Remote Similarity	NPD5281	Approved
0.6556	Remote Similarity	NPD5369	Approved
0.6552	Remote Similarity	NPD6933	Approved
0.6548	Remote Similarity	NPD4691	Approved
0.6548	Remote Similarity	NPD4747	Approved
0.6543	Remote Similarity	NPD7341	Phase 2
0.6543	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4195	Approved
0.6509	Remote Similarity	NPD5249	Phase 3
0.6509	Remote Similarity	NPD5169	Approved
0.6509	Remote Similarity	NPD5248	Approved
0.6509	Remote Similarity	NPD5250	Approved
0.6509	Remote Similarity	NPD5251	Approved
0.6509	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD7290	Approved
0.6509	Remote Similarity	NPD5247	Approved
0.6509	Remote Similarity	NPD5135	Approved
0.6509	Remote Similarity	NPD6883	Approved
0.6506	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5696	Approved
0.6477	Remote Similarity	NPD5776	Phase 2
0.6477	Remote Similarity	NPD6925	Approved
0.6471	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5276	Approved
0.6449	Remote Similarity	NPD5216	Approved
0.6449	Remote Similarity	NPD5217	Approved
0.6449	Remote Similarity	NPD6869	Approved
0.6449	Remote Similarity	NPD6847	Approved
0.6449	Remote Similarity	NPD6649	Approved
0.6449	Remote Similarity	NPD5215	Approved
0.6449	Remote Similarity	NPD8130	Phase 1
0.6449	Remote Similarity	NPD5127	Approved
0.6449	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6650	Approved
0.6449	Remote Similarity	NPD6617	Approved
0.6444	Remote Similarity	NPD7514	Phase 3
0.6444	Remote Similarity	NPD7509	Discontinued
0.6444	Remote Similarity	NPD7332	Phase 2
0.6437	Remote Similarity	NPD8039	Approved
0.6437	Remote Similarity	NPD3703	Phase 2
0.6429	Remote Similarity	NPD6922	Approved
0.6429	Remote Similarity	NPD3698	Phase 2
0.6429	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD6923	Approved
0.6421	Remote Similarity	NPD4518	Approved
0.6413	Remote Similarity	NPD7154	Phase 3
0.6413	Remote Similarity	NPD6695	Phase 3
0.6404	Remote Similarity	NPD7145	Approved
0.6392	Remote Similarity	NPD8035	Phase 2
0.6392	Remote Similarity	NPD8034	Phase 2
0.6389	Remote Similarity	NPD6882	Approved
0.6389	Remote Similarity	NPD8297	Approved
0.6383	Remote Similarity	NPD6098	Approved
0.6381	Remote Similarity	NPD6412	Phase 2

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