NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.721
LogD:	2.809
LogS:	-3.705
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.236
Fsp3:	0.867
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:	-4.779
MDCK Permeability:	1.1738304237951525e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.409
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.243
Plasma Protein Binding (PPB):	73.61893463134766%
Volume Distribution (VD):	0.928
Pgp-substrate:	26.700214385986328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.296
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.468
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	8.225
Half-life (T1/2):	0.467

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.055
Carcinogencity:	0.026
Eye Corrosion:	0.409
Eye Irritation:	0.642
Respiratory Toxicity:	0.671

Download Data

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

Natural Product: NPC60837

Natural Product ID:	NPC60837
*Common Name:**	(1R,2R,4As,5R,8Ar)-2-Isopropyl-4A-Methyl-8-Methylenedecahydronaphthalene-1,5-Diol
IUPAC Name:	(1R,2R,4aS,5R,8aR)-4a-methyl-8-methylidene-2-propan-2-yl-1,2,3,4,5,6,7,8a-octahydronaphthalene-1,5-diol
Synonyms:
Standard InCHIKey:	WKKJGHCXVKEJNU-UXXRCYHCSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-9(2)11-7-8-15(4)12(16)6-5-10(3)13(15)14(11)17/h9,11-14,16-17H,3,5-8H2,1-2,4H3/t11-,12-,13+,14-,15-/m1/s1
SMILES:	C=C1CC[C@H]([C@@]2([C@@H]1[C@H](O)[C@H](CC2)C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814427
PubChem CID:	53344589
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
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	Whole plants	Mountain Emei, Sichuan Province, China	2008-OCT	PMID[21561060]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21561060]

☑ 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
EC50	1
IC50	6
Others	2

Activity Type	# Activity
Cell Line	7
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	37000.0	nM	PMID[558494]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	35300.0	nM	PMID[558494]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	41600.0	nM	PMID[558494]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	32400.0	nM	PMID[558494]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	31100.0	nM	PMID[558494]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	28100.0	nM	PMID[558494]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	68100.0	nM	PMID[558494]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	2.1	n.a.	PMID[558494]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	31900.0	nM	PMID[558494]

☑ 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 NPC60837 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	181
0.1-0.2	1966
0.2-0.3	9258
0.3-0.4	15600
0.4-0.5	6826
0.5-0.6	5544
0.6-0.7	2648
0.7-0.8	579
0.8-0.85	65
0.85-0.9	17
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208198
1.0	High Similarity	NPC282619
1.0	High Similarity	NPC172613
1.0	High Similarity	NPC2728
1.0	High Similarity	NPC11555
0.9508	High Similarity	NPC144650
0.9508	High Similarity	NPC101128
0.9365	High Similarity	NPC185874
0.9365	High Similarity	NPC139207
0.9206	High Similarity	NPC473929
0.9062	High Similarity	NPC253303
0.9062	High Similarity	NPC269077
0.9048	High Similarity	NPC258595
0.8955	High Similarity	NPC95165
0.8939	High Similarity	NPC92801
0.8923	High Similarity	NPC276616
0.8923	High Similarity	NPC244790
0.8889	High Similarity	NPC68656
0.8689	High Similarity	NPC189290
0.8689	High Similarity	NPC474769
0.8657	High Similarity	NPC283316
0.8636	High Similarity	NPC245795
0.8615	High Similarity	NPC475897
0.8529	High Similarity	NPC167706
0.8529	High Similarity	NPC164022
0.8507	High Similarity	NPC234511
0.85	High Similarity	NPC67508
0.85	High Similarity	NPC84824
0.8429	Intermediate Similarity	NPC291503
0.8429	Intermediate Similarity	NPC3403
0.8406	Intermediate Similarity	NPC211009
0.8382	Intermediate Similarity	NPC45296
0.8361	Intermediate Similarity	NPC264779
0.8358	Intermediate Similarity	NPC266578
0.831	Intermediate Similarity	NPC14112
0.831	Intermediate Similarity	NPC86305
0.831	Intermediate Similarity	NPC63958
0.8308	Intermediate Similarity	NPC219940
0.8286	Intermediate Similarity	NPC308440
0.8286	Intermediate Similarity	NPC472503
0.8286	Intermediate Similarity	NPC477138
0.8286	Intermediate Similarity	NPC243342
0.8261	Intermediate Similarity	NPC301226
0.8261	Intermediate Similarity	NPC242001
0.8261	Intermediate Similarity	NPC111234
0.8235	Intermediate Similarity	NPC9942
0.8235	Intermediate Similarity	NPC210323
0.8219	Intermediate Similarity	NPC5604
0.8194	Intermediate Similarity	NPC471798
0.8194	Intermediate Similarity	NPC130136
0.8194	Intermediate Similarity	NPC138502
0.8194	Intermediate Similarity	NPC91594
0.8182	Intermediate Similarity	NPC300442
0.8169	Intermediate Similarity	NPC231256
0.8169	Intermediate Similarity	NPC185536
0.8169	Intermediate Similarity	NPC230704
0.8169	Intermediate Similarity	NPC240235
0.8169	Intermediate Similarity	NPC104387
0.8169	Intermediate Similarity	NPC70982
0.8169	Intermediate Similarity	NPC212879
0.8169	Intermediate Similarity	NPC178383
0.8169	Intermediate Similarity	NPC477923
0.8169	Intermediate Similarity	NPC144075
0.8169	Intermediate Similarity	NPC66566
0.8143	Intermediate Similarity	NPC182717
0.8143	Intermediate Similarity	NPC68443
0.8143	Intermediate Similarity	NPC471799
0.8116	Intermediate Similarity	NPC145498
0.8108	Intermediate Similarity	NPC78545
0.8108	Intermediate Similarity	NPC71535
0.8108	Intermediate Similarity	NPC47149
0.8088	Intermediate Similarity	NPC208999
0.8088	Intermediate Similarity	NPC2648
0.8082	Intermediate Similarity	NPC301707
0.8082	Intermediate Similarity	NPC244385
0.8082	Intermediate Similarity	NPC474989
0.8082	Intermediate Similarity	NPC138621
0.8082	Intermediate Similarity	NPC477817
0.8082	Intermediate Similarity	NPC472502
0.8082	Intermediate Similarity	NPC22955
0.8082	Intermediate Similarity	NPC99168
0.8082	Intermediate Similarity	NPC475
0.8082	Intermediate Similarity	NPC477819
0.8082	Intermediate Similarity	NPC300499
0.8082	Intermediate Similarity	NPC470396
0.8082	Intermediate Similarity	NPC6978
0.8082	Intermediate Similarity	NPC167037
0.806	Intermediate Similarity	NPC476406
0.8056	Intermediate Similarity	NPC93662
0.8056	Intermediate Similarity	NPC278091
0.8056	Intermediate Similarity	NPC91573
0.8056	Intermediate Similarity	NPC106432
0.8056	Intermediate Similarity	NPC477925
0.8056	Intermediate Similarity	NPC38141
0.8056	Intermediate Similarity	NPC265588
0.8056	Intermediate Similarity	NPC274079
0.8056	Intermediate Similarity	NPC78067
0.803	Intermediate Similarity	NPC225415
0.8028	Intermediate Similarity	NPC100334
0.8028	Intermediate Similarity	NPC25511
0.8028	Intermediate Similarity	NPC201048
0.8028	Intermediate Similarity	NPC62657
0.8028	Intermediate Similarity	NPC49168
0.8028	Intermediate Similarity	NPC254509
0.8028	Intermediate Similarity	NPC471797
0.8028	Intermediate Similarity	NPC91858
0.8028	Intermediate Similarity	NPC192638
0.8028	Intermediate Similarity	NPC145552
0.8028	Intermediate Similarity	NPC196358
0.8028	Intermediate Similarity	NPC5046
0.8028	Intermediate Similarity	NPC476366
0.8	Intermediate Similarity	NPC477792
0.8	Intermediate Similarity	NPC157655
0.8	Intermediate Similarity	NPC209318
0.8	Intermediate Similarity	NPC223330
0.8	Intermediate Similarity	NPC476646
0.8	Intermediate Similarity	NPC23954
0.8	Intermediate Similarity	NPC242992
0.7973	Intermediate Similarity	NPC472463
0.7973	Intermediate Similarity	NPC53744
0.7973	Intermediate Similarity	NPC80530
0.7973	Intermediate Similarity	NPC24504
0.7973	Intermediate Similarity	NPC470429
0.7973	Intermediate Similarity	NPC291379
0.7973	Intermediate Similarity	NPC273410
0.7945	Intermediate Similarity	NPC260301
0.7945	Intermediate Similarity	NPC202540
0.7945	Intermediate Similarity	NPC331618
0.7945	Intermediate Similarity	NPC119355
0.7945	Intermediate Similarity	NPC90979
0.7945	Intermediate Similarity	NPC157996
0.7945	Intermediate Similarity	NPC34177
0.7945	Intermediate Similarity	NPC477924
0.7945	Intermediate Similarity	NPC40394
0.7945	Intermediate Similarity	NPC248830
0.7945	Intermediate Similarity	NPC212241
0.7945	Intermediate Similarity	NPC470711
0.7945	Intermediate Similarity	NPC470758
0.7945	Intermediate Similarity	NPC307336
0.7945	Intermediate Similarity	NPC257191
0.7945	Intermediate Similarity	NPC101475
0.7945	Intermediate Similarity	NPC472805
0.7937	Intermediate Similarity	NPC236588
0.7917	Intermediate Similarity	NPC200243
0.7917	Intermediate Similarity	NPC32832
0.791	Intermediate Similarity	NPC27243
0.791	Intermediate Similarity	NPC64123
0.791	Intermediate Similarity	NPC476737
0.7887	Intermediate Similarity	NPC265485
0.7887	Intermediate Similarity	NPC474140
0.7887	Intermediate Similarity	NPC472506
0.7887	Intermediate Similarity	NPC195489
0.7887	Intermediate Similarity	NPC220939
0.7867	Intermediate Similarity	NPC102253
0.7867	Intermediate Similarity	NPC322313
0.7867	Intermediate Similarity	NPC287749
0.7867	Intermediate Similarity	NPC475679
0.7867	Intermediate Similarity	NPC236237
0.7867	Intermediate Similarity	NPC96362
0.7857	Intermediate Similarity	NPC34834
0.7838	Intermediate Similarity	NPC472342
0.7838	Intermediate Similarity	NPC196753
0.7838	Intermediate Similarity	NPC285761
0.7838	Intermediate Similarity	NPC472501
0.7838	Intermediate Similarity	NPC102708
0.7838	Intermediate Similarity	NPC230295
0.7838	Intermediate Similarity	NPC275910
0.7838	Intermediate Similarity	NPC31828
0.7838	Intermediate Similarity	NPC158662
0.7838	Intermediate Similarity	NPC98386
0.7838	Intermediate Similarity	NPC472499
0.7838	Intermediate Similarity	NPC42853
0.7838	Intermediate Similarity	NPC253807
0.7838	Intermediate Similarity	NPC472500
0.7826	Intermediate Similarity	NPC96484
0.7826	Intermediate Similarity	NPC471238
0.7808	Intermediate Similarity	NPC96319
0.7808	Intermediate Similarity	NPC265328
0.7808	Intermediate Similarity	NPC321016
0.7808	Intermediate Similarity	NPC240604
0.7808	Intermediate Similarity	NPC189883
0.7808	Intermediate Similarity	NPC106364
0.7808	Intermediate Similarity	NPC290598
0.7808	Intermediate Similarity	NPC321381
0.7808	Intermediate Similarity	NPC122418
0.7808	Intermediate Similarity	NPC300324
0.7808	Intermediate Similarity	NPC120098
0.7808	Intermediate Similarity	NPC27765
0.7808	Intermediate Similarity	NPC107059
0.7808	Intermediate Similarity	NPC73875
0.7808	Intermediate Similarity	NPC470766
0.7808	Intermediate Similarity	NPC470749
0.7808	Intermediate Similarity	NPC237460
0.7808	Intermediate Similarity	NPC30590
0.7794	Intermediate Similarity	NPC202017
0.7792	Intermediate Similarity	NPC232023
0.7778	Intermediate Similarity	NPC39068
0.7778	Intermediate Similarity	NPC306727
0.7778	Intermediate Similarity	NPC476736
0.7763	Intermediate Similarity	NPC474531

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 NPC60837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2504
0.2-0.3	4079
0.3-0.4	1717
0.4-0.5	372
0.5-0.6	206
0.6-0.7	99
0.7-0.8	16
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
0.7867	Intermediate Similarity	NPD7525	Registered
0.7808	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7645	Phase 2
0.7671	Intermediate Similarity	NPD6942	Approved
0.7671	Intermediate Similarity	NPD7339	Approved
0.7534	Intermediate Similarity	NPD6924	Approved
0.7534	Intermediate Similarity	NPD6926	Approved
0.7403	Intermediate Similarity	NPD7509	Discontinued
0.7333	Intermediate Similarity	NPD6933	Approved
0.7222	Intermediate Similarity	NPD6923	Approved
0.7222	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD3667	Approved
0.7167	Intermediate Similarity	NPD385	Approved
0.7167	Intermediate Similarity	NPD384	Approved
0.716	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7144	Approved
0.7123	Intermediate Similarity	NPD7143	Approved
0.7073	Intermediate Similarity	NPD3618	Phase 1
0.7051	Intermediate Similarity	NPD6929	Approved
0.7037	Intermediate Similarity	NPD4786	Approved
0.7027	Intermediate Similarity	NPD7151	Approved
0.7027	Intermediate Similarity	NPD7152	Approved
0.7027	Intermediate Similarity	NPD7150	Approved
0.6974	Remote Similarity	NPD8264	Approved
0.6962	Remote Similarity	NPD4748	Discontinued
0.6962	Remote Similarity	NPD6931	Approved
0.6962	Remote Similarity	NPD6930	Phase 2
0.6957	Remote Similarity	NPD368	Approved
0.6842	Remote Similarity	NPD4785	Approved
0.6842	Remote Similarity	NPD4784	Approved
0.6829	Remote Similarity	NPD3666	Approved
0.6829	Remote Similarity	NPD3665	Phase 1
0.6829	Remote Similarity	NPD3133	Approved
0.6829	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5328	Approved
0.68	Remote Similarity	NPD4243	Approved
0.6795	Remote Similarity	NPD6932	Approved
0.6795	Remote Similarity	NPD5776	Phase 2
0.6795	Remote Similarity	NPD6925	Approved
0.6786	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4202	Approved
0.6757	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7145	Approved
0.6707	Remote Similarity	NPD6695	Phase 3
0.6707	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6625	Remote Similarity	NPD6683	Phase 2
0.6548	Remote Similarity	NPD6893	Approved
0.6543	Remote Similarity	NPD7332	Phase 2
0.6543	Remote Similarity	NPD7514	Phase 3
0.6538	Remote Similarity	NPD5275	Approved
0.6538	Remote Similarity	NPD4190	Phase 3
0.6533	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4755	Approved
0.6463	Remote Similarity	NPD6902	Approved
0.6463	Remote Similarity	NPD6898	Phase 1
0.6447	Remote Similarity	NPD4787	Phase 1
0.6438	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3668	Phase 3
0.642	Remote Similarity	NPD4195	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6395	Remote Similarity	NPD7750	Discontinued
0.6395	Remote Similarity	NPD7524	Approved
0.6375	Remote Similarity	NPD6116	Phase 1
0.6374	Remote Similarity	NPD5222	Approved
0.6374	Remote Similarity	NPD5221	Approved
0.6374	Remote Similarity	NPD4697	Phase 3
0.6374	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5286	Approved
0.6344	Remote Similarity	NPD4696	Approved
0.6344	Remote Similarity	NPD4700	Approved
0.6344	Remote Similarity	NPD5285	Approved
0.6341	Remote Similarity	NPD4695	Discontinued
0.6333	Remote Similarity	NPD7748	Approved
0.6329	Remote Similarity	NPD3703	Phase 2
0.6324	Remote Similarity	NPD342	Phase 1
0.6316	Remote Similarity	NPD3698	Phase 2
0.6304	Remote Similarity	NPD7902	Approved
0.6304	Remote Similarity	NPD5173	Approved
0.6301	Remote Similarity	NPD371	Approved
0.6279	Remote Similarity	NPD5279	Phase 3
0.6277	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD6117	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6237	Remote Similarity	NPD7638	Approved
0.6237	Remote Similarity	NPD5290	Discontinued
0.6237	Remote Similarity	NPD4225	Approved
0.6234	Remote Similarity	NPD4245	Approved
0.6234	Remote Similarity	NPD4244	Approved
0.6211	Remote Similarity	NPD5226	Approved
0.6211	Remote Similarity	NPD5225	Approved
0.6211	Remote Similarity	NPD5211	Phase 2
0.6211	Remote Similarity	NPD5224	Approved
0.6211	Remote Similarity	NPD4633	Approved
0.6203	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4223	Phase 3
0.619	Remote Similarity	NPD4221	Approved
0.617	Remote Similarity	NPD7640	Approved
0.617	Remote Similarity	NPD7639	Approved
0.6146	Remote Similarity	NPD4754	Approved
0.6146	Remote Similarity	NPD5175	Approved
0.6146	Remote Similarity	NPD5174	Approved
0.6111	Remote Similarity	NPD1145	Discontinued
0.6111	Remote Similarity	NPD7087	Discontinued
0.6098	Remote Similarity	NPD6115	Approved
0.6098	Remote Similarity	NPD6118	Approved
0.6098	Remote Similarity	NPD3617	Approved
0.6098	Remote Similarity	NPD6114	Approved
0.6098	Remote Similarity	NPD6697	Approved
0.6092	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5141	Approved
0.6047	Remote Similarity	NPD4197	Approved
0.6026	Remote Similarity	NPD4789	Approved
0.602	Remote Similarity	NPD4767	Approved
0.602	Remote Similarity	NPD6675	Approved
0.602	Remote Similarity	NPD7128	Approved
0.602	Remote Similarity	NPD4768	Approved
0.602	Remote Similarity	NPD5739	Approved
0.602	Remote Similarity	NPD6402	Approved
0.5978	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7900	Approved
0.5977	Remote Similarity	NPD5329	Approved
0.5974	Remote Similarity	NPD6705	Phase 1
0.5968	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5701	Approved
0.596	Remote Similarity	NPD5697	Approved
0.5952	Remote Similarity	NPD6928	Phase 2
0.5938	Remote Similarity	NPD4159	Approved
0.5938	Remote Similarity	NPD386	Approved
0.5938	Remote Similarity	NPD388	Approved
0.5934	Remote Similarity	NPD6411	Approved
0.5914	Remote Similarity	NPD5210	Approved
0.5914	Remote Similarity	NPD4629	Approved
0.5909	Remote Similarity	NPD4138	Approved
0.5909	Remote Similarity	NPD5330	Approved
0.5909	Remote Similarity	NPD6684	Approved
0.5909	Remote Similarity	NPD4693	Phase 3
0.5909	Remote Similarity	NPD6409	Approved
0.5909	Remote Similarity	NPD4689	Approved
0.5909	Remote Similarity	NPD7146	Approved
0.5909	Remote Similarity	NPD4519	Discontinued
0.5909	Remote Similarity	NPD7521	Approved
0.5909	Remote Similarity	NPD4688	Approved
0.5909	Remote Similarity	NPD5205	Approved
0.5909	Remote Similarity	NPD7334	Approved
0.5909	Remote Similarity	NPD4690	Approved
0.5909	Remote Similarity	NPD4623	Approved
0.5904	Remote Similarity	NPD3671	Phase 1
0.59	Remote Similarity	NPD5128	Approved
0.59	Remote Similarity	NPD4729	Approved
0.59	Remote Similarity	NPD6881	Approved
0.59	Remote Similarity	NPD6011	Approved
0.59	Remote Similarity	NPD6899	Approved
0.59	Remote Similarity	NPD7320	Approved
0.59	Remote Similarity	NPD4730	Approved
0.5842	Remote Similarity	NPD6372	Approved
0.5842	Remote Similarity	NPD6014	Approved
0.5842	Remote Similarity	NPD6013	Approved
0.5842	Remote Similarity	NPD6373	Approved
0.5842	Remote Similarity	NPD6012	Approved
0.5824	Remote Similarity	NPD7136	Phase 2
0.5802	Remote Similarity	NPD1810	Approved
0.5802	Remote Similarity	NPD1811	Approved
0.5795	Remote Similarity	NPD1696	Phase 3
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5784	Remote Similarity	NPD5248	Approved
0.5784	Remote Similarity	NPD6883	Approved
0.5784	Remote Similarity	NPD5247	Approved
0.5784	Remote Similarity	NPD5135	Approved
0.5784	Remote Similarity	NPD5249	Phase 3
0.5784	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5250	Approved
0.5784	Remote Similarity	NPD5251	Approved
0.5784	Remote Similarity	NPD7290	Approved
0.5784	Remote Similarity	NPD4634	Approved
0.5784	Remote Similarity	NPD7102	Approved
0.5784	Remote Similarity	NPD5169	Approved
0.5778	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD4722	Approved
0.5778	Remote Similarity	NPD4723	Approved
0.5778	Remote Similarity	NPD6903	Approved
0.5769	Remote Similarity	NPD5360	Phase 3
0.5769	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7637	Suspended
0.5743	Remote Similarity	NPD5168	Approved
0.573	Remote Similarity	NPD5690	Phase 2
0.573	Remote Similarity	NPD5280	Approved
0.573	Remote Similarity	NPD4694	Approved
0.5728	Remote Similarity	NPD5217	Approved
0.5728	Remote Similarity	NPD6649	Approved
0.5728	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