NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	3.7
LogD:	3.779
LogS:	-4.397
# 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:	4.774
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:	-4.723
MDCK Permeability:	2.7009447876480408e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.115
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	91.32855224609375%
Volume Distribution (VD):	1.006
Pgp-substrate:	7.432823657989502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.719
CYP2C9-inhibitor:	0.174
CYP2C9-substrate:	0.535
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.364

ADMET: Excretion

Clearance (CL):	3.451
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.301
Carcinogencity:	0.049
Eye Corrosion:	0.262
Eye Irritation:	0.956
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC477138

Natural Product ID:	NPC477138
*Common Name:**	(2R,4aR,4bS,6S,7R,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-2,6-diol
IUPAC Name:	(2R,4aR,4bS,6S,7R,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-2,6-diol
Synonyms:
Standard InCHIKey:	BXDBZZUQTQKCEI-QTGPRJIVSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-19(4)12-13-7-8-15-18(2,3)16(21)9-10-20(15,5)14(13)11-17(19)22/h6,12,14-17,21-22H,1,7-11H2,2-5H3/t14-,15-,16+,17-,19+,20+/m0/s1
SMILES:	C[C@]12CC[C@H](C([C@@H]1CCC3=C[C@@]([C@H](C[C@H]23)O)(C)C=C)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	76331917
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO8960	Flueggea virosa	Species	Phyllanthaceae	Eukaryota	roots	Pingtung County, Taiwan	2011-SEP	PMID[24400834]
NPO8960	Flueggea virosa	Species	Phyllanthaceae	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
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio IC50/EC50	=	3.2	n.a.	PMID[24400834]
NPT2	Others	Unspecified		IC50	=	166900	nM	PMID[24400834]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	EC50	=	52700	nM	PMID[24400834]

☑ 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 NPC477138 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	175
0.1-0.2	1301
0.2-0.3	5693
0.3-0.4	16005
0.4-0.5	8902
0.5-0.6	5613
0.6-0.7	3492
0.7-0.8	1170
0.8-0.85	210
0.85-0.9	88
0.9-0.95	35
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC243342
0.9855	High Similarity	NPC291503
0.971	High Similarity	NPC91858
0.9706	High Similarity	NPC242001
0.9577	High Similarity	NPC471798
0.9571	High Similarity	NPC477923
0.9571	High Similarity	NPC66566
0.9565	High Similarity	NPC182717
0.9565	High Similarity	NPC471799
0.9559	High Similarity	NPC145498
0.9429	High Similarity	NPC471797
0.9306	High Similarity	NPC91594
0.9306	High Similarity	NPC477924
0.9189	High Similarity	NPC96362
0.9189	High Similarity	NPC287749
0.9178	High Similarity	NPC99168
0.9178	High Similarity	NPC470396
0.9178	High Similarity	NPC22955
0.9178	High Similarity	NPC474989
0.9167	High Similarity	NPC477925
0.9167	High Similarity	NPC265588
0.9167	High Similarity	NPC106432
0.9167	High Similarity	NPC274079
0.9155	High Similarity	NPC100334
0.9143	High Similarity	NPC110799
0.9143	High Similarity	NPC167706
0.9067	High Similarity	NPC142163
0.9067	High Similarity	NPC476646
0.9054	High Similarity	NPC291379
0.9054	High Similarity	NPC53744
0.9041	High Similarity	NPC472805
0.9041	High Similarity	NPC157996
0.9041	High Similarity	NPC101475
0.9041	High Similarity	NPC90979
0.9041	High Similarity	NPC40394
0.9041	High Similarity	NPC34177
0.9014	High Similarity	NPC68443
0.9	High Similarity	NPC92801
0.8986	High Similarity	NPC208999
0.8919	High Similarity	NPC167891
0.8919	High Similarity	NPC158662
0.8919	High Similarity	NPC300499
0.8919	High Similarity	NPC230295
0.8919	High Similarity	NPC476314
0.8919	High Similarity	NPC253807
0.8919	High Similarity	NPC98386
0.8919	High Similarity	NPC196753
0.8919	High Similarity	NPC275910
0.8919	High Similarity	NPC83351
0.8904	High Similarity	NPC106364
0.8904	High Similarity	NPC300324
0.8904	High Similarity	NPC113733
0.8904	High Similarity	NPC265328
0.8904	High Similarity	NPC134330
0.8904	High Similarity	NPC321016
0.8904	High Similarity	NPC129165
0.8904	High Similarity	NPC27765
0.8904	High Similarity	NPC120098
0.8904	High Similarity	NPC189883
0.8904	High Similarity	NPC321381
0.8904	High Similarity	NPC253190
0.8904	High Similarity	NPC107059
0.8904	High Similarity	NPC30590
0.8904	High Similarity	NPC122418
0.8904	High Similarity	NPC290598
0.8904	High Similarity	NPC240604
0.8841	High Similarity	NPC197805
0.8831	High Similarity	NPC237795
0.8831	High Similarity	NPC82538
0.8816	High Similarity	NPC249423
0.8816	High Similarity	NPC474531
0.88	High Similarity	NPC100906
0.88	High Similarity	NPC1319
0.88	High Similarity	NPC472463
0.8784	High Similarity	NPC155986
0.8784	High Similarity	NPC470711
0.8784	High Similarity	NPC130136
0.8784	High Similarity	NPC318495
0.8784	High Similarity	NPC198968
0.8784	High Similarity	NPC470758
0.8784	High Similarity	NPC214570
0.8767	High Similarity	NPC304309
0.8767	High Similarity	NPC288035
0.8767	High Similarity	NPC285893
0.8767	High Similarity	NPC230301
0.8767	High Similarity	NPC34700
0.8767	High Similarity	NPC22105
0.8767	High Similarity	NPC28657
0.8767	High Similarity	NPC471723
0.8767	High Similarity	NPC162742
0.8767	High Similarity	NPC257347
0.8767	High Similarity	NPC138374
0.8767	High Similarity	NPC141071
0.8767	High Similarity	NPC136188
0.8767	High Similarity	NPC134847
0.8701	High Similarity	NPC49964
0.8701	High Similarity	NPC248886
0.8696	High Similarity	NPC286669
0.8696	High Similarity	NPC476039
0.8696	High Similarity	NPC222366
0.8684	High Similarity	NPC236112
0.8684	High Similarity	NPC234193
0.8684	High Similarity	NPC295131
0.8684	High Similarity	NPC241290
0.8684	High Similarity	NPC164840
0.8684	High Similarity	NPC209944
0.8676	High Similarity	NPC144650
0.8676	High Similarity	NPC225415
0.8676	High Similarity	NPC290367
0.8667	High Similarity	NPC148977
0.8667	High Similarity	NPC138621
0.8667	High Similarity	NPC76931
0.8667	High Similarity	NPC244385
0.8667	High Similarity	NPC87604
0.8667	High Similarity	NPC72507
0.8667	High Similarity	NPC167037
0.8667	High Similarity	NPC6978
0.8667	High Similarity	NPC477522
0.8667	High Similarity	NPC307965
0.8667	High Similarity	NPC285761
0.8667	High Similarity	NPC18603
0.8667	High Similarity	NPC11908
0.8667	High Similarity	NPC474216
0.8667	High Similarity	NPC473943
0.8649	High Similarity	NPC470749
0.8649	High Similarity	NPC237460
0.8649	High Similarity	NPC202642
0.8649	High Similarity	NPC46160
0.8649	High Similarity	NPC470362
0.8649	High Similarity	NPC96319
0.8649	High Similarity	NPC73875
0.863	High Similarity	NPC306727
0.863	High Similarity	NPC469593
0.863	High Similarity	NPC469534
0.863	High Similarity	NPC201048
0.863	High Similarity	NPC476366
0.863	High Similarity	NPC469533
0.8611	High Similarity	NPC164022
0.8592	High Similarity	NPC9942
0.8592	High Similarity	NPC210323
0.8571	High Similarity	NPC116202
0.8571	High Similarity	NPC47761
0.8571	High Similarity	NPC470383
0.8571	High Similarity	NPC264245
0.8571	High Similarity	NPC242350
0.8553	High Similarity	NPC273410
0.8553	High Similarity	NPC143182
0.8553	High Similarity	NPC28862
0.8553	High Similarity	NPC30986
0.8553	High Similarity	NPC209430
0.8553	High Similarity	NPC80530
0.8553	High Similarity	NPC47982
0.8553	High Similarity	NPC328714
0.8553	High Similarity	NPC84694
0.8553	High Similarity	NPC81306
0.8553	High Similarity	NPC109546
0.8533	High Similarity	NPC34019
0.8514	High Similarity	NPC118508
0.8514	High Similarity	NPC121744
0.8514	High Similarity	NPC322353
0.85	High Similarity	NPC261266
0.8481	Intermediate Similarity	NPC474493
0.8481	Intermediate Similarity	NPC205845
0.8481	Intermediate Similarity	NPC470077
0.8481	Intermediate Similarity	NPC124172
0.8481	Intermediate Similarity	NPC209802
0.8481	Intermediate Similarity	NPC238992
0.8472	Intermediate Similarity	NPC34834
0.8462	Intermediate Similarity	NPC50964
0.8462	Intermediate Similarity	NPC101462
0.8462	Intermediate Similarity	NPC201852
0.8462	Intermediate Similarity	NPC218616
0.8462	Intermediate Similarity	NPC296701
0.8462	Intermediate Similarity	NPC470049
0.8462	Intermediate Similarity	NPC48362
0.8462	Intermediate Similarity	NPC47763
0.8462	Intermediate Similarity	NPC304285
0.8462	Intermediate Similarity	NPC30166
0.8462	Intermediate Similarity	NPC87489
0.8451	Intermediate Similarity	NPC32055
0.8451	Intermediate Similarity	NPC94192
0.8451	Intermediate Similarity	NPC2648
0.8442	Intermediate Similarity	NPC26117
0.8442	Intermediate Similarity	NPC322313
0.8442	Intermediate Similarity	NPC102253
0.8442	Intermediate Similarity	NPC236237
0.8442	Intermediate Similarity	NPC13554
0.8429	Intermediate Similarity	NPC149680
0.8421	Intermediate Similarity	NPC205455
0.8421	Intermediate Similarity	NPC65897
0.8421	Intermediate Similarity	NPC302041
0.8421	Intermediate Similarity	NPC85346
0.8421	Intermediate Similarity	NPC186191
0.8421	Intermediate Similarity	NPC318136
0.8421	Intermediate Similarity	NPC312328
0.8375	Intermediate Similarity	NPC157257
0.8375	Intermediate Similarity	NPC318390
0.8375	Intermediate Similarity	NPC274448
0.8356	Intermediate Similarity	NPC477792
0.8356	Intermediate Similarity	NPC242992

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 NPC477138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1583
0.2-0.3	4095
0.3-0.4	2310
0.4-0.5	598
0.5-0.6	204
0.6-0.7	145
0.7-0.8	51
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD7645	Phase 2
0.8767	High Similarity	NPD6942	Approved
0.8767	High Similarity	NPD7339	Approved
0.8649	High Similarity	NPD3701	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7525	Registered
0.8267	Intermediate Similarity	NPD8264	Approved
0.8133	Intermediate Similarity	NPD6926	Approved
0.8133	Intermediate Similarity	NPD6924	Approved
0.8108	Intermediate Similarity	NPD7151	Approved
0.8108	Intermediate Similarity	NPD7150	Approved
0.8108	Intermediate Similarity	NPD7152	Approved
0.8025	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.7973	Intermediate Similarity	NPD7144	Approved
0.7973	Intermediate Similarity	NPD7143	Approved
0.7922	Intermediate Similarity	NPD6933	Approved
0.7895	Intermediate Similarity	NPD4785	Approved
0.7895	Intermediate Similarity	NPD4784	Approved
0.7838	Intermediate Similarity	NPD6922	Approved
0.7838	Intermediate Similarity	NPD6923	Approved
0.7831	Intermediate Similarity	NPD3618	Phase 1
0.7791	Intermediate Similarity	NPD6079	Approved
0.7765	Intermediate Similarity	NPD5328	Approved
0.775	Intermediate Similarity	NPD7509	Discontinued
0.7632	Intermediate Similarity	NPD4243	Approved
0.7625	Intermediate Similarity	NPD6929	Approved
0.7595	Intermediate Similarity	NPD6932	Approved
0.7586	Intermediate Similarity	NPD7515	Phase 2
0.7531	Intermediate Similarity	NPD6931	Approved
0.7531	Intermediate Similarity	NPD4748	Discontinued
0.7531	Intermediate Similarity	NPD6930	Phase 2
0.7529	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7145	Approved
0.75	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3666	Approved
0.7381	Intermediate Similarity	NPD3133	Approved
0.7381	Intermediate Similarity	NPD3665	Phase 1
0.7375	Intermediate Similarity	NPD6925	Approved
0.7375	Intermediate Similarity	NPD5776	Phase 2
0.7317	Intermediate Similarity	NPD7332	Phase 2
0.7317	Intermediate Similarity	NPD7514	Phase 3
0.7303	Intermediate Similarity	NPD4202	Approved
0.7262	Intermediate Similarity	NPD6695	Phase 3
0.7253	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5221	Approved
0.7253	Intermediate Similarity	NPD5222	Approved
0.7229	Intermediate Similarity	NPD6902	Approved
0.7222	Intermediate Similarity	NPD7748	Approved
0.7195	Intermediate Similarity	NPD6683	Phase 2
0.7195	Intermediate Similarity	NPD4195	Approved
0.7176	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3668	Phase 3
0.7174	Intermediate Similarity	NPD5173	Approved
0.7125	Intermediate Similarity	NPD5275	Approved
0.7125	Intermediate Similarity	NPD4190	Phase 3
0.7111	Intermediate Similarity	NPD6399	Phase 3
0.7108	Intermediate Similarity	NPD4695	Discontinued
0.7097	Intermediate Similarity	NPD5290	Discontinued
0.7093	Intermediate Similarity	NPD6893	Approved
0.7093	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4697	Phase 3
0.7024	Intermediate Similarity	NPD6898	Phase 1
0.7021	Intermediate Similarity	NPD5285	Approved
0.7021	Intermediate Similarity	NPD5286	Approved
0.7021	Intermediate Similarity	NPD4696	Approved
0.7011	Intermediate Similarity	NPD5279	Phase 3
0.7	Intermediate Similarity	NPD6411	Approved
0.6989	Remote Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD7902	Approved
0.6947	Remote Similarity	NPD5223	Approved
0.6932	Remote Similarity	NPD7750	Discontinued
0.6932	Remote Similarity	NPD7524	Approved
0.6915	Remote Similarity	NPD7638	Approved
0.6905	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD368	Approved
0.6875	Remote Similarity	NPD5226	Approved
0.6875	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD5225	Approved
0.6875	Remote Similarity	NPD4633	Approved
0.6842	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD4700	Approved
0.6842	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD5175	Approved
0.6804	Remote Similarity	NPD5174	Approved
0.6778	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4753	Phase 2
0.6778	Remote Similarity	NPD6101	Approved
0.6744	Remote Similarity	NPD4221	Approved
0.6744	Remote Similarity	NPD4223	Phase 3
0.6737	Remote Similarity	NPD4225	Approved
0.6735	Remote Similarity	NPD5141	Approved
0.6709	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5329	Approved
0.67	Remote Similarity	NPD6881	Approved
0.67	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6633	Remote Similarity	NPD4754	Approved
0.663	Remote Similarity	NPD7087	Discontinued
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD4623	Approved
0.6629	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD5330	Approved
0.6629	Remote Similarity	NPD6409	Approved
0.6629	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5697	Approved
0.6596	Remote Similarity	NPD5210	Approved
0.6596	Remote Similarity	NPD4629	Approved
0.6591	Remote Similarity	NPD4197	Approved
0.6569	Remote Similarity	NPD7290	Approved
0.6569	Remote Similarity	NPD7102	Approved
0.6569	Remote Similarity	NPD6883	Approved
0.6556	Remote Similarity	NPD3573	Approved
0.6535	Remote Similarity	NPD4729	Approved
0.6535	Remote Similarity	NPD4730	Approved
0.6535	Remote Similarity	NPD7320	Approved
0.6535	Remote Similarity	NPD6011	Approved
0.6535	Remote Similarity	NPD5168	Approved
0.6528	Remote Similarity	NPD342	Phase 1
0.6522	Remote Similarity	NPD7136	Phase 2
0.6505	Remote Similarity	NPD6617	Approved
0.6505	Remote Similarity	NPD6649	Approved
0.6505	Remote Similarity	NPD6847	Approved
0.6505	Remote Similarity	NPD6650	Approved
0.6505	Remote Similarity	NPD6869	Approved
0.6505	Remote Similarity	NPD8130	Phase 1
0.65	Remote Similarity	NPD4767	Approved
0.65	Remote Similarity	NPD4768	Approved
0.6484	Remote Similarity	NPD6903	Approved
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4788	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD6012	Approved
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6373	Approved
0.6471	Remote Similarity	NPD3617	Approved
0.6458	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD6083	Phase 2
0.6452	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD7637	Suspended
0.6452	Remote Similarity	NPD8034	Phase 2
0.6444	Remote Similarity	NPD5690	Phase 2
0.6444	Remote Similarity	NPD5205	Approved
0.6444	Remote Similarity	NPD4138	Approved
0.6444	Remote Similarity	NPD4690	Approved
0.6444	Remote Similarity	NPD4689	Approved
0.6444	Remote Similarity	NPD4693	Phase 3
0.6444	Remote Similarity	NPD4688	Approved
0.6442	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD8297	Approved
0.6438	Remote Similarity	NPD4219	Approved
0.6436	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD4159	Approved
0.642	Remote Similarity	NPD4787	Phase 1
0.6413	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6051	Approved
0.6408	Remote Similarity	NPD5169	Approved
0.6408	Remote Similarity	NPD4634	Approved
0.6408	Remote Similarity	NPD5247	Approved
0.6408	Remote Similarity	NPD5248	Approved
0.6408	Remote Similarity	NPD5135	Approved
0.6408	Remote Similarity	NPD5251	Approved
0.6408	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5249	Phase 3
0.6408	Remote Similarity	NPD5250	Approved
0.6383	Remote Similarity	NPD5779	Approved
0.6383	Remote Similarity	NPD5778	Approved
0.6373	Remote Similarity	NPD5128	Approved
0.6355	Remote Similarity	NPD7115	Discovery
0.6346	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5216	Approved
0.6346	Remote Similarity	NPD5127	Approved
0.6346	Remote Similarity	NPD5217	Approved
0.6346	Remote Similarity	NPD5215	Approved
0.6341	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5737	Approved
0.6304	Remote Similarity	NPD6672	Approved
0.6304	Remote Similarity	NPD4723	Approved
0.6304	Remote Similarity	NPD4722	Approved
0.6296	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4732	Discontinued
0.6264	Remote Similarity	NPD4694	Approved
0.6264	Remote Similarity	NPD5280	Approved
0.6262	Remote Similarity	NPD6868	Approved
0.6235	Remote Similarity	NPD6117	Approved
0.6226	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD7632	Discontinued
0.619	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5167	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