NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	332.324
LogP:	5.204
LogD:	4.112
LogS:	-5.117
# Rotatable Bonds:	3
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	4.495
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.567
MDCK Permeability:	1.7655132978688926e-05
Pgp-inhibitor:	0.732
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.929
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	98.295654296875%
Volume Distribution (VD):	2.343
Pgp-substrate:	1.745444893836975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.188
CYP1A2-substrate:	0.393
CYP2C19-inhibitor:	0.308
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.29
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.691
CYP3A4-inhibitor:	0.495
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	5.339
Half-life (T1/2):	0.233

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.913
Carcinogencity:	0.353
Eye Corrosion:	0.616
Eye Irritation:	0.949
Respiratory Toxicity:	0.319

Download Data

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

Natural Product: NPC476945

Natural Product ID:	NPC476945
*Common Name:**	crotonolide G
IUPAC Name:	3-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2,5-dihydrofuran
Synonyms:
Standard InCHIKey:	JJMJYXWBOKUIKH-GTAWCEEGSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-15-6-5-7-18-19(15,3)11-8-16(2)20(18,4)12-9-17-10-13-21-14-17/h6,10,16,18H,5,7-9,11-14H2,1-4H3/t16-,18+,19+,20+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC3=CCOC3)CCC=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90676770
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO33579	Croton laui	Species	Euphorbiaceae	Eukaryota	Twigs	Hainan Province, China	n.a.	PMID[24735527]

☑ 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	2
MIC	4

Activity Type	# Activity
Cell Line	2
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>=	10000	nM	PMID[24735527]
NPT168	Cell Line	P388	Mus musculus	IC50	>=	10000	nM	PMID[24735527]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	43400	nM	PMID[24735527]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	43400	nM	PMID[24735527]
NPT2	Others	Unspecified		MIC	=	43400	nM	PMID[24735527]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	43400	nM	PMID[24735527]

☑ 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 NPC476945 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	221
0.1-0.2	1707
0.2-0.3	8764
0.3-0.4	16003
0.4-0.5	8302
0.5-0.6	5550
0.6-0.7	1922
0.7-0.8	220
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8235	Intermediate Similarity	NPC327815
0.8182	Intermediate Similarity	NPC477124
0.8182	Intermediate Similarity	NPC472440
0.8133	Intermediate Similarity	NPC242767
0.8116	Intermediate Similarity	NPC474477
0.8108	Intermediate Similarity	NPC470751
0.8108	Intermediate Similarity	NPC470750
0.8052	Intermediate Similarity	NPC471218
0.8028	Intermediate Similarity	NPC34834
0.7975	Intermediate Similarity	NPC472442
0.7949	Intermediate Similarity	NPC324243
0.7922	Intermediate Similarity	NPC474731
0.7922	Intermediate Similarity	NPC7505
0.7922	Intermediate Similarity	NPC474752
0.7922	Intermediate Similarity	NPC474759
0.7922	Intermediate Similarity	NPC82986
0.7922	Intermediate Similarity	NPC474683
0.7895	Intermediate Similarity	NPC17550
0.7895	Intermediate Similarity	NPC233295
0.7857	Intermediate Similarity	NPC69649
0.7857	Intermediate Similarity	NPC197805
0.7857	Intermediate Similarity	NPC171225
0.7857	Intermediate Similarity	NPC68703
0.7848	Intermediate Similarity	NPC318515
0.7821	Intermediate Similarity	NPC155521
0.7821	Intermediate Similarity	NPC470049
0.7808	Intermediate Similarity	NPC474743
0.7792	Intermediate Similarity	NPC195424
0.7792	Intermediate Similarity	NPC233332
0.775	Intermediate Similarity	NPC474013
0.775	Intermediate Similarity	NPC42586
0.775	Intermediate Similarity	NPC189311
0.775	Intermediate Similarity	NPC473251
0.7746	Intermediate Similarity	NPC208999
0.7746	Intermediate Similarity	NPC160209
0.7746	Intermediate Similarity	NPC216460
0.7733	Intermediate Similarity	NPC244488
0.7733	Intermediate Similarity	NPC247325
0.7722	Intermediate Similarity	NPC470046
0.7722	Intermediate Similarity	NPC470047
0.7714	Intermediate Similarity	NPC279434
0.7714	Intermediate Similarity	NPC286669
0.7714	Intermediate Similarity	NPC222366
0.7714	Intermediate Similarity	NPC476039
0.7692	Intermediate Similarity	NPC25554
0.7681	Intermediate Similarity	NPC329698
0.7654	Intermediate Similarity	NPC471219
0.7654	Intermediate Similarity	NPC118266
0.7654	Intermediate Similarity	NPC470051
0.7654	Intermediate Similarity	NPC470050
0.7654	Intermediate Similarity	NPC173917
0.7639	Intermediate Similarity	NPC474248
0.7632	Intermediate Similarity	NPC316500
0.7625	Intermediate Similarity	NPC96055
0.7625	Intermediate Similarity	NPC470077
0.7606	Intermediate Similarity	NPC114651
0.7595	Intermediate Similarity	NPC200513
0.7595	Intermediate Similarity	NPC304285
0.7571	Intermediate Similarity	NPC163678
0.7568	Intermediate Similarity	NPC474140
0.7564	Intermediate Similarity	NPC469802
0.7564	Intermediate Similarity	NPC474592
0.7531	Intermediate Similarity	NPC157257
0.7531	Intermediate Similarity	NPC274448
0.7531	Intermediate Similarity	NPC470048
0.7531	Intermediate Similarity	NPC266511
0.7531	Intermediate Similarity	NPC30984
0.75	Intermediate Similarity	NPC474193
0.75	Intermediate Similarity	NPC311070
0.75	Intermediate Similarity	NPC139785
0.75	Intermediate Similarity	NPC22611
0.75	Intermediate Similarity	NPC12283
0.75	Intermediate Similarity	NPC32055
0.75	Intermediate Similarity	NPC193198
0.75	Intermediate Similarity	NPC96484
0.747	Intermediate Similarity	NPC226863
0.747	Intermediate Similarity	NPC93411
0.7468	Intermediate Similarity	NPC14203
0.7468	Intermediate Similarity	NPC229584
0.7467	Intermediate Similarity	NPC201048
0.7467	Intermediate Similarity	NPC476366
0.7465	Intermediate Similarity	NPC149680
0.7465	Intermediate Similarity	NPC202017
0.7439	Intermediate Similarity	NPC286153
0.7436	Intermediate Similarity	NPC143182
0.7436	Intermediate Similarity	NPC81306
0.7436	Intermediate Similarity	NPC84694
0.7436	Intermediate Similarity	NPC30986
0.7436	Intermediate Similarity	NPC153987
0.7436	Intermediate Similarity	NPC209430
0.7436	Intermediate Similarity	NPC109546
0.7436	Intermediate Similarity	NPC28862
0.7436	Intermediate Similarity	NPC44083
0.7436	Intermediate Similarity	NPC47982
0.7429	Intermediate Similarity	NPC107540
0.7412	Intermediate Similarity	NPC477122
0.7407	Intermediate Similarity	NPC474047
0.7407	Intermediate Similarity	NPC46320
0.7403	Intermediate Similarity	NPC91594
0.7403	Intermediate Similarity	NPC189206
0.7403	Intermediate Similarity	NPC54996
0.7397	Intermediate Similarity	NPC471560
0.7381	Intermediate Similarity	NPC5509
0.7381	Intermediate Similarity	NPC470734
0.7381	Intermediate Similarity	NPC293044
0.7381	Intermediate Similarity	NPC177141
0.7381	Intermediate Similarity	NPC174342
0.7375	Intermediate Similarity	NPC256112
0.7368	Intermediate Similarity	NPC471468
0.7368	Intermediate Similarity	NPC230301
0.7368	Intermediate Similarity	NPC471723
0.7368	Intermediate Similarity	NPC22105
0.7368	Intermediate Similarity	NPC136188
0.7368	Intermediate Similarity	NPC134847
0.7368	Intermediate Similarity	NPC32832
0.7368	Intermediate Similarity	NPC285893
0.7368	Intermediate Similarity	NPC304309
0.7368	Intermediate Similarity	NPC28657
0.7368	Intermediate Similarity	NPC162742
0.7368	Intermediate Similarity	NPC288035
0.7368	Intermediate Similarity	NPC257347
0.7368	Intermediate Similarity	NPC141071
0.7349	Intermediate Similarity	NPC166857
0.7349	Intermediate Similarity	NPC149224
0.7349	Intermediate Similarity	NPC476948
0.7342	Intermediate Similarity	NPC234193
0.7342	Intermediate Similarity	NPC268827
0.7333	Intermediate Similarity	NPC259049
0.7333	Intermediate Similarity	NPC471799
0.7333	Intermediate Similarity	NPC182717
0.7317	Intermediate Similarity	NPC65661
0.7317	Intermediate Similarity	NPC106416
0.7317	Intermediate Similarity	NPC119001
0.7317	Intermediate Similarity	NPC35933
0.7317	Intermediate Similarity	NPC86316
0.7317	Intermediate Similarity	NPC471795
0.7313	Intermediate Similarity	NPC11130
0.7308	Intermediate Similarity	NPC167891
0.7308	Intermediate Similarity	NPC473943
0.7308	Intermediate Similarity	NPC83351
0.7308	Intermediate Similarity	NPC184737
0.7308	Intermediate Similarity	NPC474216
0.7308	Intermediate Similarity	NPC476314
0.7308	Intermediate Similarity	NPC477514
0.7308	Intermediate Similarity	NPC4827
0.7297	Intermediate Similarity	NPC475728
0.7297	Intermediate Similarity	NPC145498
0.7294	Intermediate Similarity	NPC273199
0.7294	Intermediate Similarity	NPC78973
0.7286	Intermediate Similarity	NPC283247
0.7286	Intermediate Similarity	NPC174956
0.7286	Intermediate Similarity	NPC81615
0.7284	Intermediate Similarity	NPC23748
0.7284	Intermediate Similarity	NPC470558
0.7284	Intermediate Similarity	NPC42476
0.7284	Intermediate Similarity	NPC475789
0.7284	Intermediate Similarity	NPC49208
0.7273	Intermediate Similarity	NPC321016
0.7273	Intermediate Similarity	NPC240604
0.7273	Intermediate Similarity	NPC470749
0.7273	Intermediate Similarity	NPC265588
0.7273	Intermediate Similarity	NPC202642
0.7273	Intermediate Similarity	NPC113733
0.7273	Intermediate Similarity	NPC189883
0.7273	Intermediate Similarity	NPC300324
0.7273	Intermediate Similarity	NPC134330
0.7273	Intermediate Similarity	NPC129165
0.7273	Intermediate Similarity	NPC321381
0.7273	Intermediate Similarity	NPC107059
0.7273	Intermediate Similarity	NPC470362
0.7273	Intermediate Similarity	NPC46160
0.7262	Intermediate Similarity	NPC473879
0.7262	Intermediate Similarity	NPC477128
0.7262	Intermediate Similarity	NPC24816
0.7262	Intermediate Similarity	NPC472302
0.7262	Intermediate Similarity	NPC471952
0.725	Intermediate Similarity	NPC264245
0.725	Intermediate Similarity	NPC209620
0.725	Intermediate Similarity	NPC282293
0.725	Intermediate Similarity	NPC47761
0.725	Intermediate Similarity	NPC23852
0.7241	Intermediate Similarity	NPC298973
0.7241	Intermediate Similarity	NPC104925
0.7237	Intermediate Similarity	NPC469533
0.7237	Intermediate Similarity	NPC306727
0.7237	Intermediate Similarity	NPC100334
0.7237	Intermediate Similarity	NPC471797
0.7237	Intermediate Similarity	NPC469593
0.7237	Intermediate Similarity	NPC469534
0.7229	Intermediate Similarity	NPC220478
0.7229	Intermediate Similarity	NPC102996
0.7229	Intermediate Similarity	NPC131813
0.7222	Intermediate Similarity	NPC185587
0.7222	Intermediate Similarity	NPC42630
0.7215	Intermediate Similarity	NPC327674
0.7209	Intermediate Similarity	NPC471453
0.7209	Intermediate Similarity	NPC234335
0.7209	Intermediate Similarity	NPC177641
0.7209	Intermediate Similarity	NPC190442
0.7209	Intermediate Similarity	NPC329842

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 NPC476945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	2038
0.2-0.3	4242
0.3-0.4	1972
0.4-0.5	444
0.5-0.6	199
0.6-0.7	65
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
0.7595	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6051	Approved
0.7368	Intermediate Similarity	NPD7339	Approved
0.7368	Intermediate Similarity	NPD6942	Approved
0.72	Intermediate Similarity	NPD4243	Approved
0.7051	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4784	Approved
0.7013	Intermediate Similarity	NPD4785	Approved
0.7	Intermediate Similarity	NPD7645	Phase 2
0.6944	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8039	Approved
0.6824	Remote Similarity	NPD7521	Approved
0.6824	Remote Similarity	NPD6684	Approved
0.6824	Remote Similarity	NPD6409	Approved
0.6824	Remote Similarity	NPD7146	Approved
0.6824	Remote Similarity	NPD5330	Approved
0.6824	Remote Similarity	NPD7334	Approved
0.6795	Remote Similarity	NPD6924	Approved
0.6795	Remote Similarity	NPD6926	Approved
0.6765	Remote Similarity	NPD342	Phase 1
0.6711	Remote Similarity	NPD6923	Approved
0.6711	Remote Similarity	NPD6922	Approved
0.6709	Remote Similarity	NPD8264	Approved
0.6709	Remote Similarity	NPD5275	Approved
0.6709	Remote Similarity	NPD4190	Phase 3
0.6707	Remote Similarity	NPD7525	Registered
0.6706	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6672	Approved
0.6625	Remote Similarity	NPD6933	Approved
0.6623	Remote Similarity	NPD7144	Approved
0.6623	Remote Similarity	NPD7143	Approved
0.6588	Remote Similarity	NPD4786	Approved
0.6588	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6929	Approved
0.6559	Remote Similarity	NPD7638	Approved
0.6552	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3667	Approved
0.6538	Remote Similarity	NPD7152	Approved
0.6538	Remote Similarity	NPD7150	Approved
0.6538	Remote Similarity	NPD7151	Approved
0.6506	Remote Similarity	NPD6930	Phase 2
0.6506	Remote Similarity	NPD6931	Approved
0.6489	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD7639	Approved
0.6463	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5693	Phase 1
0.6437	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD4219	Approved
0.6395	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3133	Approved
0.6395	Remote Similarity	NPD3666	Approved
0.6395	Remote Similarity	NPD3665	Phase 1
0.6395	Remote Similarity	NPD3668	Phase 3
0.6386	Remote Similarity	NPD4195	Approved
0.6374	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD7750	Discontinued
0.6364	Remote Similarity	NPD7524	Approved
0.6341	Remote Similarity	NPD6925	Approved
0.6341	Remote Similarity	NPD5776	Phase 2
0.631	Remote Similarity	NPD7332	Phase 2
0.631	Remote Similarity	NPD7509	Discontinued
0.631	Remote Similarity	NPD7514	Phase 3
0.6265	Remote Similarity	NPD7145	Approved
0.625	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4623	Approved
0.6235	Remote Similarity	NPD6902	Approved
0.6222	Remote Similarity	NPD6904	Approved
0.6222	Remote Similarity	NPD5328	Approved
0.6222	Remote Similarity	NPD6080	Approved
0.6222	Remote Similarity	NPD6673	Approved
0.6216	Remote Similarity	NPD368	Approved
0.6211	Remote Similarity	NPD4225	Approved
0.6184	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4221	Approved
0.6163	Remote Similarity	NPD4223	Phase 3
0.6154	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6932	Approved
0.6136	Remote Similarity	NPD6893	Approved
0.6136	Remote Similarity	NPD5329	Approved
0.6129	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7900	Approved
0.6129	Remote Similarity	NPD7748	Approved
0.6118	Remote Similarity	NPD4748	Discontinued
0.6111	Remote Similarity	NPD5208	Approved
0.6105	Remote Similarity	NPD6083	Phase 2
0.6105	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD7087	Discontinued
0.6087	Remote Similarity	NPD6079	Approved
0.6087	Remote Similarity	NPD6050	Approved
0.6081	Remote Similarity	NPD1145	Discontinued
0.6076	Remote Similarity	NPD4137	Phase 3
0.6067	Remote Similarity	NPD5279	Phase 3
0.6064	Remote Similarity	NPD5695	Phase 3
0.6064	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6898	Phase 1
0.6044	Remote Similarity	NPD4753	Phase 2
0.604	Remote Similarity	NPD6686	Approved
0.6023	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD3573	Approved
0.5978	Remote Similarity	NPD5692	Phase 3
0.5978	Remote Similarity	NPD5207	Approved
0.5976	Remote Similarity	NPD5733	Approved
0.5938	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7902	Approved
0.593	Remote Similarity	NPD4695	Discontinued
0.5918	Remote Similarity	NPD4159	Approved
0.5914	Remote Similarity	NPD5694	Approved
0.5914	Remote Similarity	NPD7637	Suspended
0.5914	Remote Similarity	NPD7515	Phase 2
0.5889	Remote Similarity	NPD5690	Phase 2
0.5889	Remote Similarity	NPD4688	Approved
0.5889	Remote Similarity	NPD4138	Approved
0.5889	Remote Similarity	NPD5205	Approved
0.5889	Remote Similarity	NPD4690	Approved
0.5889	Remote Similarity	NPD4689	Approved
0.5889	Remote Similarity	NPD4693	Phase 3
0.5889	Remote Similarity	NPD5280	Approved
0.5889	Remote Similarity	NPD4694	Approved
0.5882	Remote Similarity	NPD3617	Approved
0.5882	Remote Similarity	NPD8262	Approved
0.5876	Remote Similarity	NPD5696	Approved
0.5859	Remote Similarity	NPD7632	Discontinued
0.5851	Remote Similarity	NPD4202	Approved
0.5802	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6939	Phase 2
0.5795	Remote Similarity	NPD5209	Approved
0.5789	Remote Similarity	NPD5707	Approved
0.5789	Remote Similarity	NPD6001	Approved
0.5784	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4058	Approved
0.5783	Remote Similarity	NPD4687	Approved
0.5778	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4722	Approved
0.5761	Remote Similarity	NPD4723	Approved
0.5745	Remote Similarity	NPD6411	Approved
0.5741	Remote Similarity	NPD7115	Discovery
0.5732	Remote Similarity	NPD5276	Approved
0.573	Remote Similarity	NPD4788	Approved
0.5729	Remote Similarity	NPD5210	Approved
0.5729	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7328	Approved
0.5688	Remote Similarity	NPD7327	Approved
0.5686	Remote Similarity	NPD5739	Approved
0.5686	Remote Similarity	NPD6640	Phase 3
0.5686	Remote Similarity	NPD6402	Approved
0.5686	Remote Similarity	NPD6675	Approved
0.5686	Remote Similarity	NPD7128	Approved
0.5684	Remote Similarity	NPD5778	Approved
0.5684	Remote Similarity	NPD5779	Approved
0.5682	Remote Similarity	NPD4139	Approved
0.5682	Remote Similarity	NPD4692	Approved
0.5673	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.567	Remote Similarity	NPD5221	Approved
0.567	Remote Similarity	NPD4697	Phase 3
0.567	Remote Similarity	NPD5222	Approved
0.567	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6404	Discontinued
0.5647	Remote Similarity	NPD1346	Approved
0.5636	Remote Similarity	NPD7516	Approved
0.5631	Remote Similarity	NPD6412	Phase 2
0.5619	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5173	Approved
0.5612	Remote Similarity	NPD4755	Approved
0.5604	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD1696	Phase 3
0.56	Remote Similarity	NPD287	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