NPASS Compound

Structure

NPC83351 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 5.5549 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1235 0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 6 0 0 0 14 8 1 6 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 6 0 0 0 17 18 1 0 0 0 0 17 22 1 6 0 0 0 19 4 1 1 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	3.897
LogD:	3.535
LogS:	-4.745
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	4.92
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.763
MDCK Permeability:	2.044319626293145e-05
Pgp-inhibitor:	0.896
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.189

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	97.95855712890625%
Volume Distribution (VD):	1.355
Pgp-substrate:	3.596853494644165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.146
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.413
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.388

ADMET: Excretion

Clearance (CL):	2.133
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.224
Carcinogencity:	0.02
Eye Corrosion:	0.159
Eye Irritation:	0.622
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC83351

Natural Product ID:	NPC83351
*Common Name:**	Hugorosenol
IUPAC Name:	(2R,3S,4bR,7R,8aR,10aR)-7-ethenyl-1,1,4b,7-tetramethyl-3,5,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-2,3-diol
Synonyms:
Standard InCHIKey:	FPJMLNAVZWUNGU-VMCOHINHSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-19(4)9-10-20(5)13(12-19)7-8-14-15(20)11-16(21)17(22)18(14,2)3/h6,11,13-14,16-17,21-22H,1,7-10,12H2,2-5H3/t13-,14-,16+,17+,19-,20-/m1/s1
SMILES:	C=C[C@]1(C)CC[C@@]2([C@@H](C1)CC[C@@H]1C2=C[C@H](O)[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234208
PubChem CID:	24776072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	12500.0	nM	PMID[520014]

☑ 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 NPC83351 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	177
0.1-0.2	1246
0.2-0.3	5193
0.3-0.4	14915
0.4-0.5	9813
0.5-0.6	6596
0.6-0.7	3582
0.7-0.8	942
0.8-0.85	147
0.85-0.9	76
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167891
0.9324	High Similarity	NPC91594
0.9306	High Similarity	NPC471799
0.9211	High Similarity	NPC234193
0.9178	High Similarity	NPC471797
0.9103	High Similarity	NPC474634
0.9103	High Similarity	NPC317458
0.9091	High Similarity	NPC264245
0.9091	High Similarity	NPC476646
0.9079	High Similarity	NPC28862
0.9079	High Similarity	NPC47982
0.9079	High Similarity	NPC143182
0.9079	High Similarity	NPC84694
0.9079	High Similarity	NPC81306
0.9079	High Similarity	NPC109546
0.9054	High Similarity	NPC66566
0.9054	High Similarity	NPC477923
0.9028	High Similarity	NPC34834
0.8987	High Similarity	NPC185568
0.8974	High Similarity	NPC50964
0.8974	High Similarity	NPC49964
0.8961	High Similarity	NPC164840
0.8961	High Similarity	NPC209944
0.8961	High Similarity	NPC241290
0.8961	High Similarity	NPC96362
0.8947	High Similarity	NPC474216
0.8947	High Similarity	NPC476314
0.8933	High Similarity	NPC253190
0.8933	High Similarity	NPC265588
0.8933	High Similarity	NPC477925
0.8933	High Similarity	NPC274079
0.8919	High Similarity	NPC243342
0.8919	High Similarity	NPC477138
0.8904	High Similarity	NPC242001
0.8846	High Similarity	NPC47761
0.8846	High Similarity	NPC209620
0.8846	High Similarity	NPC23852
0.8831	High Similarity	NPC30986
0.8831	High Similarity	NPC209430
0.8831	High Similarity	NPC328714
0.8816	High Similarity	NPC477924
0.8816	High Similarity	NPC470758
0.8816	High Similarity	NPC470711
0.8816	High Similarity	NPC471798
0.88	High Similarity	NPC291503
0.8784	High Similarity	NPC182717
0.8767	High Similarity	NPC145498
0.875	High Similarity	NPC205845
0.875	High Similarity	NPC208999
0.8734	High Similarity	NPC189972
0.8734	High Similarity	NPC101462
0.8718	High Similarity	NPC287749
0.8718	High Similarity	NPC295131
0.8701	High Similarity	NPC11908
0.8701	High Similarity	NPC473943
0.8684	High Similarity	NPC321381
0.8684	High Similarity	NPC470749
0.8684	High Similarity	NPC247325
0.8684	High Similarity	NPC244488
0.8684	High Similarity	NPC107059
0.8684	High Similarity	NPC113733
0.8684	High Similarity	NPC321016
0.8667	High Similarity	NPC201048
0.8667	High Similarity	NPC476366
0.8667	High Similarity	NPC91858
0.8667	High Similarity	NPC306727
0.8642	High Similarity	NPC274448
0.863	High Similarity	NPC471560
0.8625	High Similarity	NPC475789
0.8611	High Similarity	NPC68703
0.8611	High Similarity	NPC69649
0.8611	High Similarity	NPC114651
0.8611	High Similarity	NPC197805
0.8608	High Similarity	NPC474759
0.8608	High Similarity	NPC249423
0.8608	High Similarity	NPC474531
0.8608	High Similarity	NPC474683
0.8608	High Similarity	NPC474752
0.8608	High Similarity	NPC7505
0.8608	High Similarity	NPC474731
0.8608	High Similarity	NPC82986
0.8571	High Similarity	NPC204188
0.8571	High Similarity	NPC329596
0.8571	High Similarity	NPC80561
0.8571	High Similarity	NPC155986
0.8571	High Similarity	NPC3345
0.8571	High Similarity	NPC318495
0.8571	High Similarity	NPC130136
0.8571	High Similarity	NPC198968
0.8571	High Similarity	NPC291484
0.8571	High Similarity	NPC11216
0.8554	High Similarity	NPC133588
0.8554	High Similarity	NPC474668
0.8553	High Similarity	NPC304309
0.8553	High Similarity	NPC162742
0.8553	High Similarity	NPC288035
0.8553	High Similarity	NPC285893
0.8553	High Similarity	NPC230301
0.8553	High Similarity	NPC22105
0.8553	High Similarity	NPC28657
0.8553	High Similarity	NPC136188
0.8553	High Similarity	NPC134847
0.8537	High Similarity	NPC261266
0.8519	High Similarity	NPC238485
0.8514	High Similarity	NPC189745
0.85	High Similarity	NPC87489
0.85	High Similarity	NPC218616
0.85	High Similarity	NPC296701
0.85	High Similarity	NPC471408
0.8493	Intermediate Similarity	NPC96484
0.8481	Intermediate Similarity	NPC236112
0.8472	Intermediate Similarity	NPC476039
0.8472	Intermediate Similarity	NPC222366
0.8472	Intermediate Similarity	NPC202017
0.8472	Intermediate Similarity	NPC286669
0.8471	Intermediate Similarity	NPC41554
0.8471	Intermediate Similarity	NPC97404
0.8462	Intermediate Similarity	NPC307965
0.8462	Intermediate Similarity	NPC87604
0.8462	Intermediate Similarity	NPC76931
0.8462	Intermediate Similarity	NPC470396
0.8462	Intermediate Similarity	NPC477522
0.8462	Intermediate Similarity	NPC474989
0.8462	Intermediate Similarity	NPC22955
0.8462	Intermediate Similarity	NPC99168
0.8462	Intermediate Similarity	NPC18603
0.8452	Intermediate Similarity	NPC477606
0.8452	Intermediate Similarity	NPC470361
0.8442	Intermediate Similarity	NPC129165
0.8442	Intermediate Similarity	NPC300324
0.8442	Intermediate Similarity	NPC96319
0.8442	Intermediate Similarity	NPC240604
0.8442	Intermediate Similarity	NPC106364
0.8442	Intermediate Similarity	NPC106432
0.8442	Intermediate Similarity	NPC134330
0.8434	Intermediate Similarity	NPC470620
0.8434	Intermediate Similarity	NPC149224
0.8421	Intermediate Similarity	NPC469533
0.8421	Intermediate Similarity	NPC469593
0.8421	Intermediate Similarity	NPC469534
0.8421	Intermediate Similarity	NPC100334
0.8415	Intermediate Similarity	NPC266511
0.8415	Intermediate Similarity	NPC157257
0.84	Intermediate Similarity	NPC110799
0.84	Intermediate Similarity	NPC471268
0.84	Intermediate Similarity	NPC471271
0.84	Intermediate Similarity	NPC167706
0.8395	Intermediate Similarity	NPC470384
0.8378	Intermediate Similarity	NPC473893
0.8378	Intermediate Similarity	NPC474248
0.8378	Intermediate Similarity	NPC9942
0.8354	Intermediate Similarity	NPC53744
0.8354	Intermediate Similarity	NPC233295
0.8354	Intermediate Similarity	NPC291379
0.8333	Intermediate Similarity	NPC157996
0.8333	Intermediate Similarity	NPC34019
0.8333	Intermediate Similarity	NPC40394
0.8333	Intermediate Similarity	NPC34177
0.8333	Intermediate Similarity	NPC67872
0.8333	Intermediate Similarity	NPC472805
0.8333	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC90979
0.8313	Intermediate Similarity	NPC152808
0.8313	Intermediate Similarity	NPC6391
0.8313	Intermediate Similarity	NPC293287
0.8312	Intermediate Similarity	NPC257347
0.8312	Intermediate Similarity	NPC171148
0.8312	Intermediate Similarity	NPC69383
0.8312	Intermediate Similarity	NPC313179
0.8312	Intermediate Similarity	NPC141071
0.8312	Intermediate Similarity	NPC32832
0.8312	Intermediate Similarity	NPC471723
0.8293	Intermediate Similarity	NPC474047
0.8293	Intermediate Similarity	NPC470077
0.8293	Intermediate Similarity	NPC238992
0.8293	Intermediate Similarity	NPC231310
0.8289	Intermediate Similarity	NPC68443
0.8289	Intermediate Similarity	NPC130665
0.8289	Intermediate Similarity	NPC220939
0.8289	Intermediate Similarity	NPC474743
0.8289	Intermediate Similarity	NPC265485
0.8272	Intermediate Similarity	NPC470049
0.8272	Intermediate Similarity	NPC47763
0.8272	Intermediate Similarity	NPC304285
0.8272	Intermediate Similarity	NPC30166
0.8272	Intermediate Similarity	NPC202389
0.8267	Intermediate Similarity	NPC92801
0.825	Intermediate Similarity	NPC474592
0.825	Intermediate Similarity	NPC26117
0.825	Intermediate Similarity	NPC13554
0.8243	Intermediate Similarity	NPC471238
0.8243	Intermediate Similarity	NPC32055
0.8235	Intermediate Similarity	NPC187785
0.8235	Intermediate Similarity	NPC259875
0.8228	Intermediate Similarity	NPC158662
0.8228	Intermediate Similarity	NPC275910
0.8228	Intermediate Similarity	NPC300499
0.8228	Intermediate Similarity	NPC253807
0.8228	Intermediate Similarity	NPC477514
0.8228	Intermediate Similarity	NPC230295

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 NPC83351 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	1488
0.2-0.3	3989
0.3-0.4	2388
0.4-0.5	695
0.5-0.6	271
0.6-0.7	109
0.7-0.8	44
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8553	High Similarity	NPD7339	Approved
0.8553	High Similarity	NPD6942	Approved
0.8442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD8264	Approved
0.8125	Intermediate Similarity	NPD7645	Phase 2
0.8	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6933	Approved
0.7857	Intermediate Similarity	NPD4786	Approved
0.7831	Intermediate Similarity	NPD3667	Approved
0.7805	Intermediate Similarity	NPD7525	Registered
0.7778	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4784	Approved
0.7722	Intermediate Similarity	NPD4785	Approved
0.7722	Intermediate Similarity	NPD6924	Approved
0.7722	Intermediate Similarity	NPD6926	Approved
0.7692	Intermediate Similarity	NPD7152	Approved
0.7692	Intermediate Similarity	NPD7151	Approved
0.7692	Intermediate Similarity	NPD7150	Approved
0.7683	Intermediate Similarity	NPD6929	Approved
0.759	Intermediate Similarity	NPD6930	Phase 2
0.759	Intermediate Similarity	NPD7332	Phase 2
0.759	Intermediate Similarity	NPD6931	Approved
0.759	Intermediate Similarity	NPD7514	Phase 3
0.7564	Intermediate Similarity	NPD7143	Approved
0.7564	Intermediate Similarity	NPD7144	Approved
0.7561	Intermediate Similarity	NPD7145	Approved
0.75	Intermediate Similarity	NPD6902	Approved
0.7468	Intermediate Similarity	NPD4243	Approved
0.7439	Intermediate Similarity	NPD6925	Approved
0.7439	Intermediate Similarity	NPD5776	Phase 2
0.7436	Intermediate Similarity	NPD6923	Approved
0.7436	Intermediate Similarity	NPD6922	Approved
0.7386	Intermediate Similarity	NPD7524	Approved
0.7326	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7253	Intermediate Similarity	NPD6079	Approved
0.7241	Intermediate Similarity	NPD3133	Approved
0.7241	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7229	Intermediate Similarity	NPD6932	Approved
0.7222	Intermediate Similarity	NPD5328	Approved
0.72	Intermediate Similarity	NPD368	Approved
0.7176	Intermediate Similarity	NPD4748	Discontinued
0.7176	Intermediate Similarity	NPD7509	Discontinued
0.7159	Intermediate Similarity	NPD6893	Approved
0.7093	Intermediate Similarity	NPD6898	Phase 1
0.7083	Intermediate Similarity	NPD342	Phase 1
0.7079	Intermediate Similarity	NPD4519	Discontinued
0.7079	Intermediate Similarity	NPD4623	Approved
0.7065	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD4195	Approved
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD7750	Discontinued
0.6989	Remote Similarity	NPD6399	Phase 3
0.6988	Remote Similarity	NPD5275	Approved
0.6988	Remote Similarity	NPD4190	Phase 3
0.6979	Remote Similarity	NPD4225	Approved
0.6907	Remote Similarity	NPD7640	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.686	Remote Similarity	NPD6683	Phase 2
0.6809	Remote Similarity	NPD4202	Approved
0.6804	Remote Similarity	NPD7638	Approved
0.6782	Remote Similarity	NPD4695	Discontinued
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5211	Phase 2
0.6757	Remote Similarity	NPD4219	Approved
0.6737	Remote Similarity	NPD7748	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6703	Remote Similarity	NPD5279	Phase 3
0.6702	Remote Similarity	NPD7637	Suspended
0.6702	Remote Similarity	NPD7087	Discontinued
0.6701	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.6633	Remote Similarity	NPD5290	Discontinued
0.6629	Remote Similarity	NPD4221	Approved
0.6629	Remote Similarity	NPD4223	Phase 3
0.6598	Remote Similarity	NPD4697	Phase 3
0.6596	Remote Similarity	NPD7136	Phase 2
0.6593	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5329	Approved
0.6585	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5286	Approved
0.6566	Remote Similarity	NPD5285	Approved
0.6566	Remote Similarity	NPD4696	Approved
0.6548	Remote Similarity	NPD4732	Discontinued
0.6531	Remote Similarity	NPD7902	Approved
0.6531	Remote Similarity	NPD4755	Approved
0.6526	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD5223	Approved
0.6495	Remote Similarity	NPD4629	Approved
0.6495	Remote Similarity	NPD5210	Approved
0.6484	Remote Similarity	NPD4197	Approved
0.6458	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD5779	Approved
0.6436	Remote Similarity	NPD5224	Approved
0.6436	Remote Similarity	NPD4633	Approved
0.6436	Remote Similarity	NPD5226	Approved
0.6436	Remote Similarity	NPD5225	Approved
0.6413	Remote Similarity	NPD1696	Phase 3
0.6404	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4700	Approved
0.6383	Remote Similarity	NPD6903	Approved
0.6383	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4788	Approved
0.6373	Remote Similarity	NPD5175	Approved
0.6373	Remote Similarity	NPD5174	Approved
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD6083	Phase 2
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3617	Approved
0.6346	Remote Similarity	NPD6412	Phase 2
0.6344	Remote Similarity	NPD5205	Approved
0.6344	Remote Similarity	NPD4138	Approved
0.6344	Remote Similarity	NPD4689	Approved
0.6344	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD4690	Approved
0.6344	Remote Similarity	NPD4693	Phase 3
0.6344	Remote Similarity	NPD5690	Phase 2
0.6337	Remote Similarity	NPD5344	Discontinued
0.6321	Remote Similarity	NPD4634	Approved
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6881	Approved
0.6286	Remote Similarity	NPD6899	Approved
0.6286	Remote Similarity	NPD6686	Approved
0.6275	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD6640	Phase 3
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD6675	Approved
0.6224	Remote Similarity	NPD7900	Approved
0.6224	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD4822	Approved
0.6222	Remote Similarity	NPD4821	Approved
0.6222	Remote Similarity	NPD4819	Approved
0.6214	Remote Similarity	NPD4754	Approved
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD4722	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6211	Remote Similarity	NPD4723	Approved
0.6204	Remote Similarity	NPD8297	Approved
0.6196	Remote Similarity	NPD5362	Discontinued
0.6196	Remote Similarity	NPD5332	Approved
0.6196	Remote Similarity	NPD5331	Approved
0.619	Remote Similarity	NPD5697	Approved
0.618	Remote Similarity	NPD4271	Approved
0.618	Remote Similarity	NPD4268	Approved
0.617	Remote Similarity	NPD5280	Approved
0.617	Remote Similarity	NPD4694	Approved
0.617	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7102	Approved
0.6168	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD4790	Discontinued
0.6147	Remote Similarity	NPD4632	Approved
0.6132	Remote Similarity	NPD6011	Approved
0.6132	Remote Similarity	NPD4729	Approved
0.6132	Remote Similarity	NPD5168	Approved
0.6132	Remote Similarity	NPD4730	Approved
0.6132	Remote Similarity	NPD7320	Approved
0.6118	Remote Similarity	NPD4787	Phase 1
0.6111	Remote Similarity	NPD6847	Approved
0.6111	Remote Similarity	NPD6649	Approved
0.6111	Remote Similarity	NPD6869	Approved
0.6111	Remote Similarity	NPD6617	Approved
0.6111	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD8130	Phase 1
0.6105	Remote Similarity	NPD3573	Approved
0.6095	Remote Similarity	NPD4767	Approved
0.6095	Remote Similarity	NPD4768	Approved
0.6091	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4270	Approved
0.6087	Remote Similarity	NPD4269	Approved
0.6087	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6013	Approved
0.6075	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6014	Approved
0.6075	Remote Similarity	NPD6012	Approved
0.6075	Remote Similarity	NPD6372	Approved
0.6075	Remote Similarity	NPD6373	Approved
0.6071	Remote Similarity	NPD7328	Approved
0.6071	Remote Similarity	NPD7327	Approved
0.6061	Remote Similarity	NPD5771	Approved
0.6058	Remote Similarity	NPD5700	Clinical (unspecified phase)

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