NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.14
Volume:	252.049
LogP:	1.176
LogD:	-0.113
LogS:	-1.245
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	4.392
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.539
MDCK Permeability:	1.8936714695882984e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.87
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	30.665584564208984%
Volume Distribution (VD):	0.917
Pgp-substrate:	72.25296783447266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.441
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	14.421
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.806
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.418
Carcinogencity:	0.894
Eye Corrosion:	0.911
Eye Irritation:	0.35
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC74995

Natural Product ID:	NPC74995
*Common Name:**	Laevinol E
IUPAC Name:	(1S,6S,8S,8aS)-1-acetyl-6-hydroxy-8,8a-dimethyl-1,3,4,6,7,8-hexahydronaphthalen-2-one
Synonyms:	Laevinol E
Standard InCHIKey:	FGCAXJRHYZZZEO-XBEUXYKBSA-N
Standard InCHI:	InChI=1S/C14H20O3/c1-8-6-11(16)7-10-4-5-12(17)13(9(2)15)14(8,10)3/h7-8,11,13,16H,4-6H2,1-3H3/t8-,11-,13-,14+/m0/s1
SMILES:	O[C@H]1C[C@H](C)[C@@]2(C(=C1)CCC(=O)[C@@H]2C(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463356
PubChem CID:	11528800
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000133] 1,3-dicarbonyl compounds [CHEMONTID:0003926] Beta-diketones

*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[450331]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[450331]

☑ 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 NPC74995 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	155
0.1-0.2	1024
0.2-0.3	4935
0.3-0.4	14403
0.4-0.5	10258
0.5-0.6	6678
0.6-0.7	3904
0.7-0.8	1216
0.8-0.85	94
0.85-0.9	20
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9459	High Similarity	NPC308038
0.9459	High Similarity	NPC152061
0.9333	High Similarity	NPC148685
0.9333	High Similarity	NPC104120
0.9333	High Similarity	NPC157895
0.9315	High Similarity	NPC263582
0.9091	High Similarity	NPC93590
0.9067	High Similarity	NPC62336
0.8974	High Similarity	NPC105173
0.8831	High Similarity	NPC172013
0.8816	High Similarity	NPC297996
0.8816	High Similarity	NPC475994
0.875	High Similarity	NPC471224
0.875	High Similarity	NPC274724
0.875	High Similarity	NPC474083
0.8701	High Similarity	NPC281138
0.8684	High Similarity	NPC203403
0.8684	High Similarity	NPC197659
0.8667	High Similarity	NPC114236
0.8649	High Similarity	NPC186042
0.8642	High Similarity	NPC472985
0.8642	High Similarity	NPC472986
0.8642	High Similarity	NPC194417
0.8642	High Similarity	NPC472974
0.8642	High Similarity	NPC470955
0.8642	High Similarity	NPC198761
0.8625	High Similarity	NPC476412
0.859	High Similarity	NPC306095
0.8571	High Similarity	NPC239098
0.8553	High Similarity	NPC470525
0.8519	High Similarity	NPC476426
0.8519	High Similarity	NPC52628
0.8481	Intermediate Similarity	NPC14151
0.8462	Intermediate Similarity	NPC7232
0.8462	Intermediate Similarity	NPC19900
0.8442	Intermediate Similarity	NPC266193
0.8442	Intermediate Similarity	NPC257666
0.8442	Intermediate Similarity	NPC325946
0.8442	Intermediate Similarity	NPC97377
0.8415	Intermediate Similarity	NPC473226
0.8415	Intermediate Similarity	NPC469994
0.8415	Intermediate Similarity	NPC322159
0.8415	Intermediate Similarity	NPC82979
0.84	Intermediate Similarity	NPC247586
0.8395	Intermediate Similarity	NPC165064
0.8395	Intermediate Similarity	NPC227132
0.8378	Intermediate Similarity	NPC34834
0.8375	Intermediate Similarity	NPC38796
0.8375	Intermediate Similarity	NPC158411
0.8375	Intermediate Similarity	NPC151519
0.8375	Intermediate Similarity	NPC212083
0.8375	Intermediate Similarity	NPC48362
0.8354	Intermediate Similarity	NPC471514
0.8354	Intermediate Similarity	NPC45495
0.8354	Intermediate Similarity	NPC2482
0.8354	Intermediate Similarity	NPC271104
0.8333	Intermediate Similarity	NPC281524
0.8333	Intermediate Similarity	NPC472983
0.8333	Intermediate Similarity	NPC472973
0.8333	Intermediate Similarity	NPC471409
0.8333	Intermediate Similarity	NPC472971
0.8333	Intermediate Similarity	NPC309603
0.8333	Intermediate Similarity	NPC473999
0.8333	Intermediate Similarity	NPC472970
0.8333	Intermediate Similarity	NPC2983
0.8333	Intermediate Similarity	NPC275494
0.8312	Intermediate Similarity	NPC472305
0.8293	Intermediate Similarity	NPC474853
0.8293	Intermediate Similarity	NPC179006
0.8289	Intermediate Similarity	NPC215050
0.8272	Intermediate Similarity	NPC169941
0.8272	Intermediate Similarity	NPC64600
0.8272	Intermediate Similarity	NPC251475
0.825	Intermediate Similarity	NPC121984
0.825	Intermediate Similarity	NPC3915
0.825	Intermediate Similarity	NPC6663
0.825	Intermediate Similarity	NPC473420
0.8243	Intermediate Similarity	NPC474248
0.8235	Intermediate Similarity	NPC48010
0.8235	Intermediate Similarity	NPC134321
0.8235	Intermediate Similarity	NPC69622
0.8228	Intermediate Similarity	NPC474113
0.8205	Intermediate Similarity	NPC34110
0.8182	Intermediate Similarity	NPC476795
0.8171	Intermediate Similarity	NPC85774
0.8171	Intermediate Similarity	NPC58841
0.8171	Intermediate Similarity	NPC329043
0.8171	Intermediate Similarity	NPC59453
0.8171	Intermediate Similarity	NPC473246
0.8171	Intermediate Similarity	NPC82902
0.8171	Intermediate Similarity	NPC221758
0.8171	Intermediate Similarity	NPC161423
0.8171	Intermediate Similarity	NPC180834
0.8171	Intermediate Similarity	NPC227064
0.8171	Intermediate Similarity	NPC40687
0.8171	Intermediate Similarity	NPC214043
0.8171	Intermediate Similarity	NPC321187
0.8148	Intermediate Similarity	NPC310989
0.8148	Intermediate Similarity	NPC103486
0.814	Intermediate Similarity	NPC116726
0.814	Intermediate Similarity	NPC473998
0.814	Intermediate Similarity	NPC475806
0.814	Intermediate Similarity	NPC472978
0.8125	Intermediate Similarity	NPC472301
0.8125	Intermediate Similarity	NPC472478
0.8118	Intermediate Similarity	NPC123912
0.8118	Intermediate Similarity	NPC473100
0.8108	Intermediate Similarity	NPC96484
0.8101	Intermediate Similarity	NPC179028
0.8101	Intermediate Similarity	NPC269543
0.8101	Intermediate Similarity	NPC247783
0.8101	Intermediate Similarity	NPC178852
0.8095	Intermediate Similarity	NPC317590
0.8095	Intermediate Similarity	NPC287079
0.8082	Intermediate Similarity	NPC202017
0.8077	Intermediate Similarity	NPC7629
0.8077	Intermediate Similarity	NPC250621
0.8077	Intermediate Similarity	NPC151622
0.8072	Intermediate Similarity	NPC474218
0.8072	Intermediate Similarity	NPC133954
0.8072	Intermediate Similarity	NPC470574
0.8068	Intermediate Similarity	NPC476245
0.8052	Intermediate Similarity	NPC470299
0.8049	Intermediate Similarity	NPC297398
0.8049	Intermediate Similarity	NPC470948
0.8049	Intermediate Similarity	NPC476082
0.8049	Intermediate Similarity	NPC215893
0.8049	Intermediate Similarity	NPC278648
0.8046	Intermediate Similarity	NPC69454
0.8046	Intermediate Similarity	NPC109305
0.8046	Intermediate Similarity	NPC472930
0.8046	Intermediate Similarity	NPC474736
0.8046	Intermediate Similarity	NPC472942
0.8025	Intermediate Similarity	NPC226068
0.8025	Intermediate Similarity	NPC136150
0.8025	Intermediate Similarity	NPC116797
0.8025	Intermediate Similarity	NPC470298
0.8023	Intermediate Similarity	NPC128672
0.8023	Intermediate Similarity	NPC320026
0.8023	Intermediate Similarity	NPC230332
0.8023	Intermediate Similarity	NPC232202
0.8023	Intermediate Similarity	NPC473099
0.8	Intermediate Similarity	NPC474854
0.8	Intermediate Similarity	NPC472490
0.8	Intermediate Similarity	NPC104560
0.8	Intermediate Similarity	NPC471560
0.7976	Intermediate Similarity	NPC31564
0.7976	Intermediate Similarity	NPC474733
0.7976	Intermediate Similarity	NPC473168
0.7976	Intermediate Similarity	NPC213412
0.7976	Intermediate Similarity	NPC327115
0.7976	Intermediate Similarity	NPC202394
0.7976	Intermediate Similarity	NPC74363
0.7976	Intermediate Similarity	NPC474732
0.7976	Intermediate Similarity	NPC474778
0.7976	Intermediate Similarity	NPC145879
0.7976	Intermediate Similarity	NPC51014
0.7976	Intermediate Similarity	NPC94666
0.7976	Intermediate Similarity	NPC475862
0.7976	Intermediate Similarity	NPC20688
0.7975	Intermediate Similarity	NPC165711
0.7975	Intermediate Similarity	NPC61952
0.7973	Intermediate Similarity	NPC68703
0.7973	Intermediate Similarity	NPC171225
0.7973	Intermediate Similarity	NPC69649
0.7955	Intermediate Similarity	NPC472977
0.7955	Intermediate Similarity	NPC8993
0.7955	Intermediate Similarity	NPC472976
0.7955	Intermediate Similarity	NPC196227
0.7952	Intermediate Similarity	NPC473157
0.7952	Intermediate Similarity	NPC237712
0.7952	Intermediate Similarity	NPC470812
0.7931	Intermediate Similarity	NPC63748
0.7931	Intermediate Similarity	NPC233116
0.7931	Intermediate Similarity	NPC472975
0.7927	Intermediate Similarity	NPC73882
0.7922	Intermediate Similarity	NPC29542
0.7922	Intermediate Similarity	NPC323437
0.7922	Intermediate Similarity	NPC201562
0.7922	Intermediate Similarity	NPC275098
0.7922	Intermediate Similarity	NPC35656
0.7907	Intermediate Similarity	NPC214387
0.7907	Intermediate Similarity	NPC5509
0.7882	Intermediate Similarity	NPC272039
0.7882	Intermediate Similarity	NPC58063
0.7882	Intermediate Similarity	NPC475740
0.7882	Intermediate Similarity	NPC90652
0.7882	Intermediate Similarity	NPC136548
0.7882	Intermediate Similarity	NPC220930
0.7882	Intermediate Similarity	NPC298904
0.7882	Intermediate Similarity	NPC312561
0.7882	Intermediate Similarity	NPC73064
0.7875	Intermediate Similarity	NPC198240
0.7875	Intermediate Similarity	NPC321514
0.7867	Intermediate Similarity	NPC471238
0.7867	Intermediate Similarity	NPC45264
0.7867	Intermediate Similarity	NPC117804
0.7865	Intermediate Similarity	NPC472932
0.7865	Intermediate Similarity	NPC134067
0.7865	Intermediate Similarity	NPC259286

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 NPC74995 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1453
0.2-0.3	3865
0.3-0.4	2495
0.4-0.5	727
0.5-0.6	233
0.6-0.7	209
0.7-0.8	22
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
0.8375	Intermediate Similarity	NPD3667	Approved
0.8171	Intermediate Similarity	NPD3666	Approved
0.8171	Intermediate Similarity	NPD4786	Approved
0.8171	Intermediate Similarity	NPD3133	Approved
0.8171	Intermediate Similarity	NPD3665	Phase 1
0.7976	Intermediate Similarity	NPD3618	Phase 1
0.7976	Intermediate Similarity	NPD5279	Phase 3
0.7765	Intermediate Similarity	NPD4519	Discontinued
0.7765	Intermediate Similarity	NPD4623	Approved
0.7701	Intermediate Similarity	NPD5328	Approved
0.7683	Intermediate Similarity	NPD4695	Discontinued
0.7529	Intermediate Similarity	NPD3668	Phase 3
0.7528	Intermediate Similarity	NPD6079	Approved
0.7528	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7444	Intermediate Similarity	NPD4202	Approved
0.7439	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4197	Approved
0.7284	Intermediate Similarity	NPD8264	Approved
0.7253	Intermediate Similarity	NPD6399	Phase 3
0.7241	Intermediate Similarity	NPD5329	Approved
0.7229	Intermediate Similarity	NPD3617	Approved
0.7204	Intermediate Similarity	NPD5221	Approved
0.7204	Intermediate Similarity	NPD5222	Approved
0.7204	Intermediate Similarity	NPD4697	Phase 3
0.7204	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5211	Phase 2
0.7174	Intermediate Similarity	NPD7748	Approved
0.7159	Intermediate Similarity	NPD4694	Approved
0.7159	Intermediate Similarity	NPD7146	Approved
0.7159	Intermediate Similarity	NPD7521	Approved
0.7159	Intermediate Similarity	NPD5280	Approved
0.7159	Intermediate Similarity	NPD7334	Approved
0.7159	Intermediate Similarity	NPD4693	Phase 3
0.7159	Intermediate Similarity	NPD4690	Approved
0.7159	Intermediate Similarity	NPD4138	Approved
0.7159	Intermediate Similarity	NPD5205	Approved
0.7159	Intermediate Similarity	NPD4688	Approved
0.7159	Intermediate Similarity	NPD4689	Approved
0.7159	Intermediate Similarity	NPD5690	Phase 2
0.7159	Intermediate Similarity	NPD6409	Approved
0.7159	Intermediate Similarity	NPD6684	Approved
0.7159	Intermediate Similarity	NPD5330	Approved
0.7128	Intermediate Similarity	NPD5173	Approved
0.7128	Intermediate Similarity	NPD4755	Approved
0.7097	Intermediate Similarity	NPD4629	Approved
0.7097	Intermediate Similarity	NPD5210	Approved
0.7093	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6942	Approved
0.7073	Intermediate Similarity	NPD7339	Approved
0.7067	Intermediate Similarity	NPD368	Approved
0.7065	Intermediate Similarity	NPD5779	Approved
0.7065	Intermediate Similarity	NPD5778	Approved
0.7045	Intermediate Similarity	NPD1696	Phase 3
0.7045	Intermediate Similarity	NPD1694	Approved
0.7041	Intermediate Similarity	NPD5141	Approved
0.7011	Intermediate Similarity	NPD4788	Approved
0.7	Intermediate Similarity	NPD6903	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5286	Approved
0.6979	Remote Similarity	NPD4700	Approved
0.6979	Remote Similarity	NPD4696	Approved
0.6979	Remote Similarity	NPD5285	Approved
0.6977	Remote Similarity	NPD4692	Approved
0.6977	Remote Similarity	NPD4139	Approved
0.6966	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6411	Approved
0.6951	Remote Similarity	NPD6926	Approved
0.6951	Remote Similarity	NPD6924	Approved
0.6947	Remote Similarity	NPD6084	Phase 2
0.6947	Remote Similarity	NPD6083	Phase 2
0.6947	Remote Similarity	NPD7902	Approved
0.6944	Remote Similarity	NPD342	Phase 1
0.6941	Remote Similarity	NPD6929	Approved
0.6941	Remote Similarity	NPD7645	Phase 2
0.6923	Remote Similarity	NPD7331	Phase 2
0.6915	Remote Similarity	NPD5695	Phase 3
0.6907	Remote Similarity	NPD5223	Approved
0.6897	Remote Similarity	NPD4270	Approved
0.6897	Remote Similarity	NPD4269	Approved
0.6889	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4137	Phase 3
0.686	Remote Similarity	NPD6931	Approved
0.686	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6930	Phase 2
0.6854	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4096	Approved
0.6837	Remote Similarity	NPD5226	Approved
0.6837	Remote Similarity	NPD4633	Approved
0.6837	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD5225	Approved
0.6824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5362	Discontinued
0.6813	Remote Similarity	NPD6672	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6804	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD7639	Approved
0.6795	Remote Similarity	NPD7341	Phase 2
0.6795	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4691	Approved
0.679	Remote Similarity	NPD4747	Approved
0.6786	Remote Similarity	NPD6933	Approved
0.6774	Remote Similarity	NPD5281	Approved
0.6774	Remote Similarity	NPD5284	Approved
0.6768	Remote Similarity	NPD5174	Approved
0.6768	Remote Similarity	NPD4754	Approved
0.6768	Remote Similarity	NPD5175	Approved
0.675	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4195	Approved
0.6739	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6101	Approved
0.6739	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5276	Approved
0.6706	Remote Similarity	NPD6925	Approved
0.6706	Remote Similarity	NPD5776	Phase 2
0.6701	Remote Similarity	NPD4225	Approved
0.6701	Remote Similarity	NPD5696	Approved
0.6701	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6922	Approved
0.6634	Remote Similarity	NPD4768	Approved
0.6634	Remote Similarity	NPD6675	Approved
0.6634	Remote Similarity	NPD6402	Approved
0.6634	Remote Similarity	NPD7128	Approved
0.6634	Remote Similarity	NPD5739	Approved
0.6634	Remote Similarity	NPD4767	Approved
0.6632	Remote Similarity	NPD7900	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4518	Approved
0.6629	Remote Similarity	NPD6695	Phase 3
0.6629	Remote Similarity	NPD7154	Phase 3
0.6628	Remote Similarity	NPD7145	Approved
0.6596	Remote Similarity	NPD7637	Suspended
0.6593	Remote Similarity	NPD6098	Approved
0.6593	Remote Similarity	NPD5786	Approved
0.6591	Remote Similarity	NPD6902	Approved
0.6585	Remote Similarity	NPD7143	Approved
0.6585	Remote Similarity	NPD4244	Approved
0.6585	Remote Similarity	NPD4245	Approved
0.6585	Remote Similarity	NPD7144	Approved
0.6569	Remote Similarity	NPD5701	Approved
0.6569	Remote Similarity	NPD6412	Phase 2
0.6569	Remote Similarity	NPD5697	Approved
0.6556	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4687	Approved
0.6548	Remote Similarity	NPD4058	Approved
0.6548	Remote Similarity	NPD5733	Approved
0.6526	Remote Similarity	NPD5133	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6506	Remote Similarity	NPD7151	Approved
0.6506	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7150	Approved
0.6506	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4243	Approved
0.6506	Remote Similarity	NPD7152	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD5168	Approved
0.6505	Remote Similarity	NPD4729	Approved
0.6505	Remote Similarity	NPD4730	Approved
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD5128	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.6505	Remote Similarity	NPD7320	Approved
0.6505	Remote Similarity	NPD6686	Approved
0.6484	Remote Similarity	NPD6893	Approved
0.6481	Remote Similarity	NPD7115	Discovery
0.6477	Remote Similarity	NPD4819	Approved
0.6477	Remote Similarity	NPD4820	Approved
0.6477	Remote Similarity	NPD5368	Approved
0.6477	Remote Similarity	NPD7509	Discontinued
0.6477	Remote Similarity	NPD4822	Approved
0.6477	Remote Similarity	NPD4821	Approved
0.6465	Remote Similarity	NPD6404	Discontinued
0.6452	Remote Similarity	NPD5208	Approved
0.6447	Remote Similarity	NPD287	Approved
0.6444	Remote Similarity	NPD5332	Approved
0.6444	Remote Similarity	NPD5331	Approved
0.6442	Remote Similarity	NPD6373	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6372	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD4268	Approved
0.6437	Remote Similarity	NPD4271	Approved
0.6421	Remote Similarity	NPD5693	Phase 1
0.6404	Remote Similarity	NPD4790	Discontinued
0.6404	Remote Similarity	NPD6898	Phase 1

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