NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.17
Volume:	271.981
LogP:	1.042
LogD:	1.442
LogS:	-2.46
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	4.846
Fsp3:	0.733
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:	-5.064
MDCK Permeability:	7.021714736765716e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.684

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	44.79657745361328%
Volume Distribution (VD):	0.941
Pgp-substrate:	64.83343505859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.434
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.751
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	4.75
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.614
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.874
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.398
Carcinogencity:	0.951
Eye Corrosion:	0.014
Eye Irritation:	0.79
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC276616

Natural Product ID:	NPC276616
*Common Name:**	3Alpha,7Alpha,12-Trihydroxyeudesm-4(15),11(13)-Diene
IUPAC Name:	(2S,4aS,6S,8aS)-6-(3-hydroxyprop-1-en-2-yl)-8a-methyl-4-methylidene-2,3,4a,5,7,8-hexahydro-1H-naphthalene-2,6-diol
Synonyms:
Standard InCHIKey:	FWFIRFWQECUTFI-AJNGGQMLSA-N
Standard InCHI:	InChI=1S/C15H24O3/c1-10-6-12(17)7-14(3)4-5-15(18,8-13(10)14)11(2)9-16/h12-13,16-18H,1-2,4-9H2,3H3/t12-,13-,14-,15-/m0/s1
SMILES:	C=C1C[C@@H](C[C@]2(C)CC[C@](C[C@@H]12)(C(=C)CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463132
PubChem CID:	11345767
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921425]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9587	Saussurea laniceps	Species	Asteraceae	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
Others	8

Activity Type	# Activity
NON-MOLECULAR	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	39.78	cpm	PMID[475324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	31.53	cpm	PMID[475324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	28.32	cpm	PMID[475324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	12.13	cpm	PMID[475324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	36.12	cpm	PMID[475324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	33.65	cpm	PMID[475324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	31.83	cpm	PMID[475324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	17.21	cpm	PMID[475324]

☑ 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 NPC276616 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	192
0.1-0.2	1829
0.2-0.3	7628
0.3-0.4	16404
0.4-0.5	7424
0.5-0.6	5797
0.6-0.7	2734
0.7-0.8	603
0.8-0.85	56
0.85-0.9	21
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9385	High Similarity	NPC245795
0.9365	High Similarity	NPC68656
0.9219	High Similarity	NPC258595
0.9104	High Similarity	NPC283316
0.9077	High Similarity	NPC475897
0.9062	High Similarity	NPC101128
0.9062	High Similarity	NPC144650
0.8955	High Similarity	NPC9942
0.8939	High Similarity	NPC139207
0.8939	High Similarity	NPC269077
0.8939	High Similarity	NPC185874
0.8939	High Similarity	NPC253303
0.8923	High Similarity	NPC282619
0.8923	High Similarity	NPC60837
0.8923	High Similarity	NPC172613
0.8923	High Similarity	NPC208198
0.8923	High Similarity	NPC2728
0.8923	High Similarity	NPC11555
0.8806	High Similarity	NPC266578
0.8806	High Similarity	NPC244790
0.8788	High Similarity	NPC473929
0.8676	High Similarity	NPC234511
0.8571	High Similarity	NPC95165
0.8571	High Similarity	NPC220939
0.8571	High Similarity	NPC265485
0.8507	High Similarity	NPC476406
0.8493	Intermediate Similarity	NPC472501
0.8472	Intermediate Similarity	NPC265588
0.8451	Intermediate Similarity	NPC476366
0.8451	Intermediate Similarity	NPC201048
0.8451	Intermediate Similarity	NPC476736
0.8429	Intermediate Similarity	NPC167706
0.8356	Intermediate Similarity	NPC260301
0.8356	Intermediate Similarity	NPC470711
0.8356	Intermediate Similarity	NPC307336
0.8356	Intermediate Similarity	NPC470758
0.8333	Intermediate Similarity	NPC185536
0.8333	Intermediate Similarity	NPC144075
0.8286	Intermediate Similarity	NPC92801
0.8281	Intermediate Similarity	NPC189290
0.8281	Intermediate Similarity	NPC474769
0.8261	Intermediate Similarity	NPC96484
0.8254	Intermediate Similarity	NPC264779
0.8243	Intermediate Similarity	NPC301707
0.8243	Intermediate Similarity	NPC472342
0.8219	Intermediate Similarity	NPC63958
0.8219	Intermediate Similarity	NPC470749
0.8219	Intermediate Similarity	NPC38141
0.8194	Intermediate Similarity	NPC471797
0.8194	Intermediate Similarity	NPC306727
0.8169	Intermediate Similarity	NPC164022
0.8169	Intermediate Similarity	NPC477792
0.8169	Intermediate Similarity	NPC23954
0.8158	Intermediate Similarity	NPC157655
0.8143	Intermediate Similarity	NPC210323
0.8133	Intermediate Similarity	NPC5604
0.8133	Intermediate Similarity	NPC476316
0.8108	Intermediate Similarity	NPC331618
0.8108	Intermediate Similarity	NPC91594
0.8108	Intermediate Similarity	NPC119355
0.8108	Intermediate Similarity	NPC248830
0.8108	Intermediate Similarity	NPC257191
0.8108	Intermediate Similarity	NPC138502
0.8108	Intermediate Similarity	NPC212241
0.8082	Intermediate Similarity	NPC32832
0.8082	Intermediate Similarity	NPC3403
0.8056	Intermediate Similarity	NPC211009
0.8056	Intermediate Similarity	NPC472506
0.8056	Intermediate Similarity	NPC471799
0.8052	Intermediate Similarity	NPC155521
0.8028	Intermediate Similarity	NPC34834
0.8028	Intermediate Similarity	NPC45296
0.8026	Intermediate Similarity	NPC47149
0.8026	Intermediate Similarity	NPC209944
0.8026	Intermediate Similarity	NPC164840
0.8026	Intermediate Similarity	NPC241290
0.8	Intermediate Similarity	NPC2648
0.8	Intermediate Similarity	NPC476314
0.8	Intermediate Similarity	NPC471238
0.8	Intermediate Similarity	NPC167891
0.8	Intermediate Similarity	NPC472500
0.8	Intermediate Similarity	NPC31828
0.8	Intermediate Similarity	NPC83351
0.8	Intermediate Similarity	NPC474216
0.8	Intermediate Similarity	NPC208999
0.8	Intermediate Similarity	NPC472499
0.7973	Intermediate Similarity	NPC91573
0.7973	Intermediate Similarity	NPC93662
0.7973	Intermediate Similarity	NPC78067
0.7973	Intermediate Similarity	NPC253190
0.7973	Intermediate Similarity	NPC278091
0.7971	Intermediate Similarity	NPC202017
0.7945	Intermediate Similarity	NPC469534
0.7945	Intermediate Similarity	NPC308440
0.7945	Intermediate Similarity	NPC472503
0.7945	Intermediate Similarity	NPC243342
0.7945	Intermediate Similarity	NPC469593
0.7945	Intermediate Similarity	NPC91858
0.7945	Intermediate Similarity	NPC477138
0.7945	Intermediate Similarity	NPC469533
0.7941	Intermediate Similarity	NPC219940
0.7922	Intermediate Similarity	NPC249423
0.7922	Intermediate Similarity	NPC476646
0.7922	Intermediate Similarity	NPC264245
0.7917	Intermediate Similarity	NPC164045
0.7917	Intermediate Similarity	NPC301226
0.7917	Intermediate Similarity	NPC242992
0.7917	Intermediate Similarity	NPC471272
0.7917	Intermediate Similarity	NPC242001
0.7917	Intermediate Similarity	NPC111234
0.791	Intermediate Similarity	NPC41160
0.7895	Intermediate Similarity	NPC30986
0.7895	Intermediate Similarity	NPC81306
0.7895	Intermediate Similarity	NPC24504
0.7895	Intermediate Similarity	NPC291379
0.7895	Intermediate Similarity	NPC209430
0.7895	Intermediate Similarity	NPC28862
0.7895	Intermediate Similarity	NPC53744
0.7895	Intermediate Similarity	NPC47982
0.7895	Intermediate Similarity	NPC143182
0.7895	Intermediate Similarity	NPC109546
0.7895	Intermediate Similarity	NPC84694
0.7887	Intermediate Similarity	NPC474248
0.7875	Intermediate Similarity	NPC6391
0.7867	Intermediate Similarity	NPC198968
0.7867	Intermediate Similarity	NPC318495
0.7867	Intermediate Similarity	NPC477924
0.7867	Intermediate Similarity	NPC169994
0.7867	Intermediate Similarity	NPC471798
0.7867	Intermediate Similarity	NPC155986
0.7857	Intermediate Similarity	NPC69649
0.7857	Intermediate Similarity	NPC74885
0.7857	Intermediate Similarity	NPC308522
0.7857	Intermediate Similarity	NPC101307
0.7857	Intermediate Similarity	NPC88454
0.7857	Intermediate Similarity	NPC68703
0.7857	Intermediate Similarity	NPC117607
0.7848	Intermediate Similarity	NPC205845
0.7848	Intermediate Similarity	NPC256567
0.7838	Intermediate Similarity	NPC104387
0.7838	Intermediate Similarity	NPC178383
0.7838	Intermediate Similarity	NPC70982
0.7838	Intermediate Similarity	NPC133580
0.7838	Intermediate Similarity	NPC231256
0.7838	Intermediate Similarity	NPC66566
0.7838	Intermediate Similarity	NPC291503
0.7838	Intermediate Similarity	NPC477923
0.7838	Intermediate Similarity	NPC212879
0.7838	Intermediate Similarity	NPC240235
0.7838	Intermediate Similarity	NPC230704
0.7826	Intermediate Similarity	NPC64123
0.7821	Intermediate Similarity	NPC218616
0.7821	Intermediate Similarity	NPC296701
0.7821	Intermediate Similarity	NPC101462
0.7821	Intermediate Similarity	NPC49964
0.7812	Intermediate Similarity	NPC67508
0.7812	Intermediate Similarity	NPC84824
0.7808	Intermediate Similarity	NPC68443
0.7808	Intermediate Similarity	NPC195489
0.7808	Intermediate Similarity	NPC182717
0.7792	Intermediate Similarity	NPC234193
0.7792	Intermediate Similarity	NPC295131
0.7792	Intermediate Similarity	NPC96362
0.7778	Intermediate Similarity	NPC145498
0.7763	Intermediate Similarity	NPC475
0.7763	Intermediate Similarity	NPC230295
0.7763	Intermediate Similarity	NPC470396
0.7763	Intermediate Similarity	NPC99168
0.7763	Intermediate Similarity	NPC42853
0.7763	Intermediate Similarity	NPC253807
0.7763	Intermediate Similarity	NPC473943
0.7763	Intermediate Similarity	NPC472502
0.7763	Intermediate Similarity	NPC11908
0.7763	Intermediate Similarity	NPC474989
0.7763	Intermediate Similarity	NPC22955
0.7763	Intermediate Similarity	NPC52755
0.7763	Intermediate Similarity	NPC196753
0.7763	Intermediate Similarity	NPC98386
0.7763	Intermediate Similarity	NPC285761
0.7763	Intermediate Similarity	NPC158662
0.7733	Intermediate Similarity	NPC321381
0.7733	Intermediate Similarity	NPC321016
0.7733	Intermediate Similarity	NPC477925
0.7733	Intermediate Similarity	NPC86305
0.7733	Intermediate Similarity	NPC470766
0.7733	Intermediate Similarity	NPC96319
0.7733	Intermediate Similarity	NPC274079
0.7733	Intermediate Similarity	NPC14112
0.7733	Intermediate Similarity	NPC107059
0.7722	Intermediate Similarity	NPC475789
0.7722	Intermediate Similarity	NPC243347
0.7722	Intermediate Similarity	NPC474634
0.7722	Intermediate Similarity	NPC232023
0.7722	Intermediate Similarity	NPC317458
0.7703	Intermediate Similarity	NPC25511
0.7703	Intermediate Similarity	NPC196358
0.7703	Intermediate Similarity	NPC254509
0.7703	Intermediate Similarity	NPC62657
0.7703	Intermediate Similarity	NPC5046
0.7703	Intermediate Similarity	NPC71152

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 NPC276616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2391
0.2-0.3	4046
0.3-0.4	1825
0.4-0.5	394
0.5-0.6	229
0.6-0.7	79
0.7-0.8	24
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
0.7733	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7645	Phase 2
0.76	Intermediate Similarity	NPD6942	Approved
0.76	Intermediate Similarity	NPD7339	Approved
0.7564	Intermediate Similarity	NPD7525	Registered
0.7564	Intermediate Similarity	NPD6931	Approved
0.7564	Intermediate Similarity	NPD6930	Phase 2
0.7467	Intermediate Similarity	NPD6924	Approved
0.7467	Intermediate Similarity	NPD6926	Approved
0.7436	Intermediate Similarity	NPD6929	Approved
0.7368	Intermediate Similarity	NPD8264	Approved
0.7349	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD6933	Approved
0.7195	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5776	Phase 2
0.7179	Intermediate Similarity	NPD6925	Approved
0.716	Intermediate Similarity	NPD3667	Approved
0.7125	Intermediate Similarity	NPD7509	Discontinued
0.7125	Intermediate Similarity	NPD4748	Discontinued
0.7125	Intermediate Similarity	NPD7332	Phase 2
0.7125	Intermediate Similarity	NPD7514	Phase 3
0.7108	Intermediate Similarity	NPD6893	Approved
0.7089	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7145	Approved
0.7037	Intermediate Similarity	NPD6898	Phase 1
0.6988	Remote Similarity	NPD4786	Approved
0.6974	Remote Similarity	NPD7152	Approved
0.6974	Remote Similarity	NPD7150	Approved
0.6974	Remote Similarity	NPD7151	Approved
0.6962	Remote Similarity	NPD6932	Approved
0.6941	Remote Similarity	NPD7750	Discontinued
0.6941	Remote Similarity	NPD7524	Approved
0.6933	Remote Similarity	NPD6923	Approved
0.6933	Remote Similarity	NPD6922	Approved
0.6933	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD368	Approved
0.6842	Remote Similarity	NPD7143	Approved
0.6842	Remote Similarity	NPD7144	Approved
0.6829	Remote Similarity	NPD6902	Approved
0.6824	Remote Similarity	NPD3618	Phase 1
0.6795	Remote Similarity	NPD4785	Approved
0.6795	Remote Similarity	NPD4784	Approved
0.679	Remote Similarity	NPD6683	Phase 2
0.6753	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6629	Remote Similarity	NPD7087	Discontinued
0.6623	Remote Similarity	NPD4787	Phase 1
0.6591	Remote Similarity	NPD5328	Approved
0.6588	Remote Similarity	NPD3665	Phase 1
0.6588	Remote Similarity	NPD3666	Approved
0.6588	Remote Similarity	NPD3133	Approved
0.6562	Remote Similarity	NPD385	Approved
0.6562	Remote Similarity	NPD384	Approved
0.6559	Remote Similarity	NPD4225	Approved
0.6556	Remote Similarity	NPD4202	Approved
0.6526	Remote Similarity	NPD5211	Phase 2
0.6522	Remote Similarity	NPD342	Phase 1
0.65	Remote Similarity	NPD4190	Phase 3
0.65	Remote Similarity	NPD5275	Approved
0.6494	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4755	Approved
0.6444	Remote Similarity	NPD6079	Approved
0.6444	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD4753	Phase 2
0.6395	Remote Similarity	NPD3668	Phase 3
0.6392	Remote Similarity	NPD5141	Approved
0.6386	Remote Similarity	NPD4195	Approved
0.6329	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD1696	Phase 3
0.6316	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6316	Remote Similarity	NPD7640	Approved
0.6316	Remote Similarity	NPD7639	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.6301	Remote Similarity	NPD1145	Discontinued
0.6267	Remote Similarity	NPD371	Approved
0.6264	Remote Similarity	NPD8034	Phase 2
0.6264	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD4732	Discontinued
0.625	Remote Similarity	NPD4159	Approved
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4623	Approved
0.6211	Remote Similarity	NPD7638	Approved
0.6196	Remote Similarity	NPD6399	Phase 3
0.6186	Remote Similarity	NPD5224	Approved
0.6186	Remote Similarity	NPD5225	Approved
0.6186	Remote Similarity	NPD5226	Approved
0.6186	Remote Similarity	NPD4633	Approved
0.6184	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4697	Phase 3
0.617	Remote Similarity	NPD5221	Approved
0.617	Remote Similarity	NPD5222	Approved
0.6163	Remote Similarity	NPD4223	Phase 3
0.6163	Remote Similarity	NPD4221	Approved
0.6154	Remote Similarity	NPD388	Approved
0.6154	Remote Similarity	NPD386	Approved
0.6154	Remote Similarity	NPD7136	Phase 2
0.6129	Remote Similarity	NPD7748	Approved
0.6122	Remote Similarity	NPD5174	Approved
0.6122	Remote Similarity	NPD5175	Approved
0.6118	Remote Similarity	NPD4695	Discontinued
0.6105	Remote Similarity	NPD5173	Approved
0.6098	Remote Similarity	NPD3703	Phase 2
0.6087	Remote Similarity	NPD7637	Suspended
0.6082	Remote Similarity	NPD5223	Approved
0.6076	Remote Similarity	NPD3698	Phase 2
0.6067	Remote Similarity	NPD5279	Phase 3
0.6064	Remote Similarity	NPD4629	Approved
0.6064	Remote Similarity	NPD5210	Approved
0.6042	Remote Similarity	NPD5290	Discontinued
0.6024	Remote Similarity	NPD6117	Approved
0.6023	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD4245	Approved
0.6	Remote Similarity	NPD6402	Approved
0.596	Remote Similarity	NPD4754	Approved
0.5955	Remote Similarity	NPD5329	Approved
0.5952	Remote Similarity	NPD6116	Phase 1
0.5949	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD5360	Phase 3
0.5941	Remote Similarity	NPD5697	Approved
0.5941	Remote Similarity	NPD5701	Approved
0.5938	Remote Similarity	NPD6083	Phase 2
0.5938	Remote Similarity	NPD7902	Approved
0.5938	Remote Similarity	NPD6084	Phase 2
0.5914	Remote Similarity	NPD6411	Approved
0.5889	Remote Similarity	NPD4688	Approved
0.5889	Remote Similarity	NPD5205	Approved
0.5889	Remote Similarity	NPD4138	Approved
0.5889	Remote Similarity	NPD4689	Approved
0.5889	Remote Similarity	NPD4690	Approved
0.5889	Remote Similarity	NPD4693	Phase 3
0.5889	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7115	Discovery
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD6697	Approved
0.5882	Remote Similarity	NPD6118	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD6115	Approved
0.5882	Remote Similarity	NPD3617	Approved
0.5882	Remote Similarity	NPD3671	Phase 1
0.5882	Remote Similarity	NPD4729	Approved
0.5882	Remote Similarity	NPD6114	Approved
0.587	Remote Similarity	NPD6051	Approved
0.5859	Remote Similarity	NPD7632	Discontinued
0.5851	Remote Similarity	NPD5778	Approved
0.5851	Remote Similarity	NPD5779	Approved
0.5825	Remote Similarity	NPD6373	Approved
0.5825	Remote Similarity	NPD6013	Approved
0.5825	Remote Similarity	NPD6014	Approved
0.5825	Remote Similarity	NPD6012	Approved
0.5825	Remote Similarity	NPD6372	Approved
0.5802	Remote Similarity	NPD4789	Approved
0.5769	Remote Similarity	NPD5250	Approved
0.5769	Remote Similarity	NPD5247	Approved
0.5769	Remote Similarity	NPD4634	Approved
0.5769	Remote Similarity	NPD5248	Approved
0.5769	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD5249	Phase 3
0.5769	Remote Similarity	NPD6883	Approved
0.5769	Remote Similarity	NPD7290	Approved
0.5769	Remote Similarity	NPD5251	Approved
0.5761	Remote Similarity	NPD4722	Approved
0.5761	Remote Similarity	NPD4723	Approved
0.5758	Remote Similarity	NPD5344	Discontinued
0.5755	Remote Similarity	NPD8133	Approved
0.5753	Remote Similarity	NPD4219	Approved
0.575	Remote Similarity	NPD6705	Phase 1
0.5747	Remote Similarity	NPD4821	Approved
0.5747	Remote Similarity	NPD4822	Approved
0.5747	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6928	Phase 2
0.5747	Remote Similarity	NPD4820	Approved
0.5747	Remote Similarity	NPD4819	Approved
0.5732	Remote Similarity	NPD4758	Discontinued
0.5729	Remote Similarity	NPD5695	Phase 3
0.5728	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD5280	Approved
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD5690	Phase 2
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD4694	Approved
0.5714	Remote Similarity	NPD5215	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