NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.16
Volume:	248.765
LogP:	1.489
LogD:	1.322
LogS:	-3.026
# Rotatable Bonds:	1
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	5.117
Fsp3:	0.929
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:	-4.558
MDCK Permeability:	1.8677159459912218e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.697
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.102
30% Bioavailability (F30%):	0.602

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.955
Plasma Protein Binding (PPB):	19.084877014160156%
Volume Distribution (VD):	1.506
Pgp-substrate:	66.33271789550781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.712
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.725
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	13.799
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.406
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.482
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.745
Carcinogencity:	0.579
Eye Corrosion:	0.965
Eye Irritation:	0.916
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: NPC475725

Natural Product ID:	NPC475725
*Common Name:**	Laevinol H
IUPAC Name:	1-[(1aS,4S,4aS,5R,6R,8aR)-6-hydroxy-4,4a-dimethyl-1a,2,3,4,5,6,7,8-octahydronaphtho[4a,5-b]oxiren-5-yl]ethanone
Synonyms:	Laevinol H
Standard InCHIKey:	RAAOQGUCUAQLHJ-YNGKBFMNSA-N
Standard InCHI:	InChI=1S/C14H22O3/c1-8-4-5-11-14(17-11)7-6-10(16)12(9(2)15)13(8,14)3/h8,10-12,16H,4-7H2,1-3H3/t8-,10+,11-,12-,13-,14-/m0/s1
SMILES:	O[C@@H]1CC[C@]23[C@@]([C@H]1C(=O)C)(C)[C@@H](C)CC[C@@H]3O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512947
PubChem CID:	5326390
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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[573537]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[573537]

☑ 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 NPC475725 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	431
0.1-0.2	3498
0.2-0.3	9353
0.3-0.4	14498
0.4-0.5	7059
0.5-0.6	6053
0.6-0.7	1649
0.7-0.8	143
0.8-0.85	2
0.85-0.9	5
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC474215
0.9	High Similarity	NPC475729
0.8987	High Similarity	NPC475689
0.8831	High Similarity	NPC275243
0.8554	High Similarity	NPC477614
0.8554	High Similarity	NPC226491
0.8395	Intermediate Similarity	NPC227170
0.8108	Intermediate Similarity	NPC472984
0.809	Intermediate Similarity	NPC477264
0.8072	Intermediate Similarity	NPC477434
0.8023	Intermediate Similarity	NPC477440
0.8023	Intermediate Similarity	NPC477443
0.7978	Intermediate Similarity	NPC17336
0.7976	Intermediate Similarity	NPC473350
0.7931	Intermediate Similarity	NPC477442
0.7931	Intermediate Similarity	NPC477433
0.7931	Intermediate Similarity	NPC477444
0.7875	Intermediate Similarity	NPC307865
0.7875	Intermediate Similarity	NPC143250
0.7857	Intermediate Similarity	NPC237938
0.7857	Intermediate Similarity	NPC219535
0.7857	Intermediate Similarity	NPC50438
0.7848	Intermediate Similarity	NPC159789
0.7816	Intermediate Similarity	NPC67653
0.7816	Intermediate Similarity	NPC471459
0.7816	Intermediate Similarity	NPC61688
0.7802	Intermediate Similarity	NPC190080
0.7802	Intermediate Similarity	NPC111187
0.7778	Intermediate Similarity	NPC478084
0.7765	Intermediate Similarity	NPC477205
0.775	Intermediate Similarity	NPC474020
0.7738	Intermediate Similarity	NPC15091
0.7711	Intermediate Similarity	NPC50658
0.7701	Intermediate Similarity	NPC473319
0.7701	Intermediate Similarity	NPC471221
0.7701	Intermediate Similarity	NPC131104
0.7701	Intermediate Similarity	NPC3032
0.7674	Intermediate Similarity	NPC248216
0.7674	Intermediate Similarity	NPC120395
0.7674	Intermediate Similarity	NPC83242
0.7647	Intermediate Similarity	NPC34984
0.7647	Intermediate Similarity	NPC25037
0.7614	Intermediate Similarity	NPC200580
0.759	Intermediate Similarity	NPC125366
0.759	Intermediate Similarity	NPC134227
0.7586	Intermediate Similarity	NPC263802
0.7556	Intermediate Similarity	NPC476189
0.7531	Intermediate Similarity	NPC472487
0.7531	Intermediate Similarity	NPC472486
0.7529	Intermediate Similarity	NPC472847
0.7528	Intermediate Similarity	NPC475211
0.7528	Intermediate Similarity	NPC88337
0.7527	Intermediate Similarity	NPC476294
0.75	Intermediate Similarity	NPC236459
0.75	Intermediate Similarity	NPC475743
0.75	Intermediate Similarity	NPC254123
0.75	Intermediate Similarity	NPC476379
0.75	Intermediate Similarity	NPC90676
0.7471	Intermediate Similarity	NPC477441
0.7471	Intermediate Similarity	NPC80700
0.7468	Intermediate Similarity	NPC89310
0.7442	Intermediate Similarity	NPC471044
0.7442	Intermediate Similarity	NPC473336
0.7439	Intermediate Similarity	NPC475031
0.7407	Intermediate Similarity	NPC35871
0.7407	Intermediate Similarity	NPC125767
0.7407	Intermediate Similarity	NPC21220
0.7407	Intermediate Similarity	NPC68565
0.7391	Intermediate Similarity	NPC62407
0.7391	Intermediate Similarity	NPC287354
0.7386	Intermediate Similarity	NPC202937
0.7386	Intermediate Similarity	NPC470920
0.7381	Intermediate Similarity	NPC477851
0.7375	Intermediate Similarity	NPC109510
0.7375	Intermediate Similarity	NPC474755
0.7363	Intermediate Similarity	NPC147272
0.7356	Intermediate Similarity	NPC477445
0.7326	Intermediate Similarity	NPC269684
0.7312	Intermediate Similarity	NPC163685
0.7312	Intermediate Similarity	NPC235109
0.7312	Intermediate Similarity	NPC193785
0.7308	Intermediate Similarity	NPC474954
0.7303	Intermediate Similarity	NPC163296
0.7294	Intermediate Similarity	NPC469745
0.7294	Intermediate Similarity	NPC476071
0.7292	Intermediate Similarity	NPC471254
0.7284	Intermediate Similarity	NPC168511
0.7284	Intermediate Similarity	NPC159325
0.7284	Intermediate Similarity	NPC133922
0.7284	Intermediate Similarity	NPC55508
0.7283	Intermediate Similarity	NPC309127
0.7283	Intermediate Similarity	NPC247877
0.7283	Intermediate Similarity	NPC191094
0.7283	Intermediate Similarity	NPC470424
0.7283	Intermediate Similarity	NPC302008
0.7273	Intermediate Similarity	NPC476727
0.7273	Intermediate Similarity	NPC302111
0.7273	Intermediate Similarity	NPC476717
0.7273	Intermediate Similarity	NPC476726
0.7253	Intermediate Similarity	NPC52756
0.7253	Intermediate Similarity	NPC216137
0.7245	Intermediate Similarity	NPC470587
0.7241	Intermediate Similarity	NPC181871
0.7241	Intermediate Similarity	NPC65133
0.7241	Intermediate Similarity	NPC9060
0.7241	Intermediate Similarity	NPC291310
0.7241	Intermediate Similarity	NPC473299
0.7229	Intermediate Similarity	NPC221420
0.7229	Intermediate Similarity	NPC23884
0.7222	Intermediate Similarity	NPC56962
0.7222	Intermediate Similarity	NPC24705
0.7216	Intermediate Similarity	NPC471253
0.7215	Intermediate Similarity	NPC327728
0.7215	Intermediate Similarity	NPC6120
0.7215	Intermediate Similarity	NPC131892
0.7215	Intermediate Similarity	NPC213178
0.7209	Intermediate Similarity	NPC268040
0.7204	Intermediate Similarity	NPC231060
0.7204	Intermediate Similarity	NPC82633
0.7204	Intermediate Similarity	NPC138245
0.7204	Intermediate Similarity	NPC84018
0.7195	Intermediate Similarity	NPC273366
0.7195	Intermediate Similarity	NPC179858
0.7191	Intermediate Similarity	NPC298904
0.7191	Intermediate Similarity	NPC239938
0.7188	Intermediate Similarity	NPC475958
0.7179	Intermediate Similarity	NPC41542
0.7179	Intermediate Similarity	NPC329466
0.7179	Intermediate Similarity	NPC328304
0.7174	Intermediate Similarity	NPC474379
0.716	Intermediate Similarity	NPC81759
0.716	Intermediate Similarity	NPC282905
0.716	Intermediate Similarity	NPC477229
0.716	Intermediate Similarity	NPC68426
0.716	Intermediate Similarity	NPC232112
0.7159	Intermediate Similarity	NPC474572
0.7158	Intermediate Similarity	NPC253995
0.7158	Intermediate Similarity	NPC471038
0.7143	Intermediate Similarity	NPC77756
0.7143	Intermediate Similarity	NPC472146
0.7143	Intermediate Similarity	NPC476296
0.7143	Intermediate Similarity	NPC80401
0.7143	Intermediate Similarity	NPC185529
0.7126	Intermediate Similarity	NPC217559
0.7126	Intermediate Similarity	NPC327451
0.7126	Intermediate Similarity	NPC292458
0.7126	Intermediate Similarity	NPC268578
0.7111	Intermediate Similarity	NPC476435
0.7108	Intermediate Similarity	NPC108840
0.7108	Intermediate Similarity	NPC475742
0.7108	Intermediate Similarity	NPC78935
0.7108	Intermediate Similarity	NPC5767
0.7097	Intermediate Similarity	NPC477495
0.7097	Intermediate Similarity	NPC103527
0.7093	Intermediate Similarity	NPC48756
0.7093	Intermediate Similarity	NPC58631
0.7093	Intermediate Similarity	NPC328639
0.7093	Intermediate Similarity	NPC280781
0.7093	Intermediate Similarity	NPC329490
0.7083	Intermediate Similarity	NPC471269
0.7079	Intermediate Similarity	NPC472272
0.7073	Intermediate Similarity	NPC317212
0.7065	Intermediate Similarity	NPC476168
0.7065	Intermediate Similarity	NPC475878
0.7065	Intermediate Similarity	NPC474065
0.7059	Intermediate Similarity	NPC201276
0.7059	Intermediate Similarity	NPC320144
0.7059	Intermediate Similarity	NPC80891
0.7053	Intermediate Similarity	NPC136781
0.7045	Intermediate Similarity	NPC105895
0.7045	Intermediate Similarity	NPC97505
0.7045	Intermediate Similarity	NPC319909
0.7045	Intermediate Similarity	NPC474996
0.7041	Intermediate Similarity	NPC473406
0.7041	Intermediate Similarity	NPC87927
0.7041	Intermediate Similarity	NPC34562
0.7037	Intermediate Similarity	NPC247195
0.7037	Intermediate Similarity	NPC151018
0.7037	Intermediate Similarity	NPC58057
0.7037	Intermediate Similarity	NPC320549
0.7037	Intermediate Similarity	NPC156277
0.7037	Intermediate Similarity	NPC473267
0.7021	Intermediate Similarity	NPC41070
0.7021	Intermediate Similarity	NPC98639
0.7021	Intermediate Similarity	NPC90014
0.7021	Intermediate Similarity	NPC470232
0.7011	Intermediate Similarity	NPC61107
0.7011	Intermediate Similarity	NPC317066
0.7011	Intermediate Similarity	NPC289486
0.7011	Intermediate Similarity	NPC271163
0.701	Intermediate Similarity	NPC298266
0.701	Intermediate Similarity	NPC14634
0.701	Intermediate Similarity	NPC259654
0.701	Intermediate Similarity	NPC46848
0.7	Intermediate Similarity	NPC473165
0.7	Intermediate Similarity	NPC259009
0.7	Intermediate Similarity	NPC153604
0.6989	Remote Similarity	NPC199543
0.6989	Remote Similarity	NPC144739
0.6989	Remote Similarity	NPC59170

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 NPC475725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	541
0.1-0.2	3749
0.2-0.3	3215
0.3-0.4	1061
0.4-0.5	317
0.5-0.6	234
0.6-0.7	32
0.7-0.8	1
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
0.7848	Intermediate Similarity	NPD3703	Phase 2
0.7215	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD1700	Approved
0.6941	Remote Similarity	NPD6114	Approved
0.6941	Remote Similarity	NPD6115	Approved
0.6941	Remote Similarity	NPD6697	Approved
0.6941	Remote Similarity	NPD6118	Approved
0.6931	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6116	Phase 1
0.679	Remote Similarity	NPD3698	Phase 2
0.6707	Remote Similarity	NPD4244	Approved
0.6707	Remote Similarity	NPD4245	Approved
0.6706	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3702	Approved
0.6552	Remote Similarity	NPD3671	Phase 1
0.6506	Remote Similarity	NPD4789	Approved
0.6429	Remote Similarity	NPD4758	Discontinued
0.6375	Remote Similarity	NPD371	Approved
0.6344	Remote Similarity	NPD3618	Phase 1
0.6316	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD6008	Approved
0.6235	Remote Similarity	NPD5777	Approved
0.6226	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4224	Phase 2
0.62	Remote Similarity	NPD4755	Approved
0.6195	Remote Similarity	NPD6921	Approved
0.6186	Remote Similarity	NPD8034	Phase 2
0.6186	Remote Similarity	NPD8035	Phase 2
0.6186	Remote Similarity	NPD6079	Approved
0.6168	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1780	Approved
0.6154	Remote Similarity	NPD1779	Approved
0.6154	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4202	Approved
0.61	Remote Similarity	NPD4697	Phase 3
0.6095	Remote Similarity	NPD5739	Approved
0.6095	Remote Similarity	NPD6675	Approved
0.6095	Remote Similarity	NPD6402	Approved
0.6095	Remote Similarity	NPD7128	Approved
0.6087	Remote Similarity	NPD3667	Approved
0.6078	Remote Similarity	NPD5286	Approved
0.6078	Remote Similarity	NPD4700	Approved
0.6078	Remote Similarity	NPD4696	Approved
0.6078	Remote Similarity	NPD5285	Approved
0.6075	Remote Similarity	NPD6373	Approved
0.6075	Remote Similarity	NPD6372	Approved
0.6071	Remote Similarity	NPD229	Approved
0.6064	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7902	Approved
0.6038	Remote Similarity	NPD5701	Approved
0.6038	Remote Similarity	NPD5697	Approved
0.6019	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5364	Discontinued
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6881	Approved
0.5981	Remote Similarity	NPD6011	Approved
0.5981	Remote Similarity	NPD6899	Approved
0.5981	Remote Similarity	NPD7320	Approved
0.5965	Remote Similarity	NPD6319	Approved
0.5965	Remote Similarity	NPD6054	Approved
0.5965	Remote Similarity	NPD6059	Approved
0.5963	Remote Similarity	NPD6650	Approved
0.5963	Remote Similarity	NPD6649	Approved
0.5962	Remote Similarity	NPD5225	Approved
0.5962	Remote Similarity	NPD4633	Approved
0.5962	Remote Similarity	NPD5226	Approved
0.5962	Remote Similarity	NPD5224	Approved
0.5962	Remote Similarity	NPD5211	Phase 2
0.596	Remote Similarity	NPD6399	Phase 3
0.5957	Remote Similarity	NPD4786	Approved
0.5941	Remote Similarity	NPD5222	Approved
0.5941	Remote Similarity	NPD5221	Approved
0.5941	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6014	Approved
0.5926	Remote Similarity	NPD6012	Approved
0.5926	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6013	Approved
0.5913	Remote Similarity	NPD6015	Approved
0.5913	Remote Similarity	NPD6016	Approved
0.5905	Remote Similarity	NPD5174	Approved
0.5905	Remote Similarity	NPD4754	Approved
0.5905	Remote Similarity	NPD5175	Approved
0.59	Remote Similarity	NPD7748	Approved
0.5888	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5173	Approved
0.5872	Remote Similarity	NPD6883	Approved
0.5872	Remote Similarity	NPD7290	Approved
0.5872	Remote Similarity	NPD7102	Approved
0.587	Remote Similarity	NPD6928	Phase 2
0.5862	Remote Similarity	NPD5988	Approved
0.5862	Remote Similarity	NPD6370	Approved
0.5862	Remote Similarity	NPD6081	Approved
0.5859	Remote Similarity	NPD7515	Phase 2
0.5859	Remote Similarity	NPD6411	Approved
0.5856	Remote Similarity	NPD4632	Approved
0.5851	Remote Similarity	NPD4788	Approved
0.5851	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD3669	Approved
0.5849	Remote Similarity	NPD5141	Approved
0.5844	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7115	Discovery
0.5818	Remote Similarity	NPD6617	Approved
0.5818	Remote Similarity	NPD6847	Approved
0.5818	Remote Similarity	NPD6869	Approved
0.5818	Remote Similarity	NPD8130	Phase 1
0.5818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD8328	Phase 3
0.58	Remote Similarity	NPD5778	Approved
0.58	Remote Similarity	NPD5779	Approved
0.5794	Remote Similarity	NPD4768	Approved
0.5794	Remote Similarity	NPD4767	Approved
0.5789	Remote Similarity	NPD3665	Phase 1
0.5789	Remote Similarity	NPD3666	Approved
0.5789	Remote Similarity	NPD3133	Approved
0.5773	Remote Similarity	NPD3573	Approved
0.5766	Remote Similarity	NPD6882	Approved
0.5766	Remote Similarity	NPD8297	Approved
0.5763	Remote Similarity	NPD7492	Approved
0.5753	Remote Similarity	NPD384	Approved
0.5753	Remote Similarity	NPD385	Approved
0.5747	Remote Similarity	NPD4787	Phase 1
0.5743	Remote Similarity	NPD7900	Approved
0.5743	Remote Similarity	NPD5282	Discontinued
0.5743	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.573	Remote Similarity	NPD1811	Approved
0.573	Remote Similarity	NPD1810	Approved
0.5714	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6616	Approved
0.5702	Remote Similarity	NPD6009	Approved
0.5688	Remote Similarity	NPD5128	Approved
0.5688	Remote Similarity	NPD4730	Approved
0.5688	Remote Similarity	NPD4729	Approved
0.5678	Remote Similarity	NPD7604	Phase 2
0.5673	Remote Similarity	NPD4225	Approved
0.5673	Remote Similarity	NPD7638	Approved
0.5667	Remote Similarity	NPD8293	Discontinued
0.5667	Remote Similarity	NPD7078	Approved
0.5657	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6101	Approved
0.5641	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5983	Phase 2
0.562	Remote Similarity	NPD6033	Approved
0.562	Remote Similarity	NPD7736	Approved
0.5619	Remote Similarity	NPD7640	Approved
0.5619	Remote Similarity	NPD7639	Approved
0.5619	Remote Similarity	NPD8418	Phase 2
0.5616	Remote Similarity	NPD388	Approved
0.5616	Remote Similarity	NPD386	Approved
0.5614	Remote Similarity	NPD6274	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