NPASS Compound

Structure

NPC471798 OpenBabel07101718312D 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 -1.0000 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 0.8660 1.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 2 0 0 0 0 8 17 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 16 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 11 1 6 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 6 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:	4.137
LogD:	3.73
LogS:	-4.707
# 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:	4.899
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.669
MDCK Permeability:	2.173633583879564e-05
Pgp-inhibitor:	0.953
Pgp-substrate:	0.098
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.613
Plasma Protein Binding (PPB):	93.80974578857422%
Volume Distribution (VD):	1.606
Pgp-substrate:	8.989758491516113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.332
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.297
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.419

ADMET: Excretion

Clearance (CL):	5.257
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.562
Carcinogencity:	0.163
Eye Corrosion:	0.671
Eye Irritation:	0.644
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: NPC471798

Natural Product ID:	NPC471798
*Common Name:**	Ebractenoid D
IUPAC Name:	(2S,4bR,7R,8aR,9S,10aR)-7-ethenyl-1,1,4b,7-tetramethyl-3,5,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-2,9-diol
Synonyms:
Standard InCHIKey:	IKYRTDCRZLGSRA-JRNUACSKSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-19(4)9-10-20(5)13-7-8-17(22)18(2,3)14(13)11-16(21)15(20)12-19/h6-7,14-17,21-22H,1,8-12H2,2-5H3/t14-,15+,16+,17+,19-,20+/m1/s1
SMILES:	CC1(C(CC=C2C1CC(C3C2(CCC(C3)(C)C=C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234215
PubChem CID:	90670338
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	=	5510.0	nM	PMID[449332]

☑ 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 NPC471798 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	178
0.1-0.2	1368
0.2-0.3	5570
0.3-0.4	15364
0.4-0.5	9119
0.5-0.6	5708
0.6-0.7	3952
0.7-0.8	1150
0.8-0.85	213
0.85-0.9	42
0.9-0.95	31
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC243342
0.9577	High Similarity	NPC477138
0.9467	High Similarity	NPC476646
0.9444	High Similarity	NPC291503
0.9437	High Similarity	NPC182717
0.9437	High Similarity	NPC471799
0.9333	High Similarity	NPC96362
0.9333	High Similarity	NPC287749
0.9306	High Similarity	NPC471797
0.9306	High Similarity	NPC91858
0.9296	High Similarity	NPC242001
0.92	High Similarity	NPC472463
0.9189	High Similarity	NPC91594
0.9189	High Similarity	NPC130136
0.9178	High Similarity	NPC66566
0.9178	High Similarity	NPC477923
0.9155	High Similarity	NPC145498
0.9091	High Similarity	NPC248886
0.9067	High Similarity	NPC470396
0.9067	High Similarity	NPC22955
0.9067	High Similarity	NPC99168
0.9067	High Similarity	NPC87604
0.9067	High Similarity	NPC148977
0.9067	High Similarity	NPC474989
0.9054	High Similarity	NPC265588
0.9054	High Similarity	NPC253190
0.9054	High Similarity	NPC106432
0.9041	High Similarity	NPC100334
0.9028	High Similarity	NPC167706
0.9028	High Similarity	NPC110799
0.8961	High Similarity	NPC242350
0.8961	High Similarity	NPC470383
0.8961	High Similarity	NPC249423
0.8947	High Similarity	NPC291379
0.8947	High Similarity	NPC53744
0.8933	High Similarity	NPC101475
0.8933	High Similarity	NPC40394
0.8933	High Similarity	NPC34177
0.8933	High Similarity	NPC477924
0.8933	High Similarity	NPC472805
0.8933	High Similarity	NPC157996
0.8933	High Similarity	NPC90979
0.8889	High Similarity	NPC92801
0.8875	High Similarity	NPC261266
0.8873	High Similarity	NPC208999
0.8861	High Similarity	NPC209802
0.8861	High Similarity	NPC124172
0.8861	High Similarity	NPC474493
0.8846	High Similarity	NPC50964
0.8831	High Similarity	NPC26117
0.8816	High Similarity	NPC98386
0.8816	High Similarity	NPC253807
0.8816	High Similarity	NPC83351
0.8816	High Similarity	NPC300499
0.8816	High Similarity	NPC167891
0.8816	High Similarity	NPC158662
0.8816	High Similarity	NPC196753
0.8816	High Similarity	NPC230295
0.8816	High Similarity	NPC275910
0.88	High Similarity	NPC113733
0.88	High Similarity	NPC134330
0.88	High Similarity	NPC321381
0.88	High Similarity	NPC27765
0.88	High Similarity	NPC290598
0.88	High Similarity	NPC122418
0.88	High Similarity	NPC265328
0.88	High Similarity	NPC189883
0.88	High Similarity	NPC321016
0.88	High Similarity	NPC30590
0.88	High Similarity	NPC120098
0.88	High Similarity	NPC274079
0.88	High Similarity	NPC106364
0.88	High Similarity	NPC240604
0.88	High Similarity	NPC129165
0.88	High Similarity	NPC477925
0.88	High Similarity	NPC107059
0.88	High Similarity	NPC300324
0.8784	High Similarity	NPC306727
0.8734	High Similarity	NPC477818
0.8734	High Similarity	NPC237795
0.8734	High Similarity	NPC82538
0.8732	High Similarity	NPC197805
0.8718	High Similarity	NPC23852
0.8718	High Similarity	NPC209620
0.8718	High Similarity	NPC474531
0.8718	High Similarity	NPC142163
0.8701	High Similarity	NPC1319
0.8684	High Similarity	NPC318495
0.8684	High Similarity	NPC155986
0.8684	High Similarity	NPC198968
0.8684	High Similarity	NPC470711
0.8684	High Similarity	NPC470758
0.8684	High Similarity	NPC214570
0.8667	High Similarity	NPC28657
0.8667	High Similarity	NPC141071
0.8667	High Similarity	NPC285893
0.8667	High Similarity	NPC134847
0.8667	High Similarity	NPC34700
0.8667	High Similarity	NPC32832
0.8667	High Similarity	NPC304309
0.8667	High Similarity	NPC22105
0.8667	High Similarity	NPC136188
0.8667	High Similarity	NPC162742
0.8667	High Similarity	NPC257347
0.8667	High Similarity	NPC288035
0.8667	High Similarity	NPC230301
0.8667	High Similarity	NPC138374
0.8667	High Similarity	NPC471723
0.8649	High Similarity	NPC68443
0.8642	High Similarity	NPC6391
0.8642	High Similarity	NPC237344
0.8642	High Similarity	NPC24277
0.8642	High Similarity	NPC94462
0.8625	High Similarity	NPC127606
0.8625	High Similarity	NPC475798
0.8608	High Similarity	NPC49964
0.8608	High Similarity	NPC470614
0.8608	High Similarity	NPC1272
0.8592	High Similarity	NPC476039
0.8592	High Similarity	NPC222366
0.8592	High Similarity	NPC286669
0.859	High Similarity	NPC295131
0.859	High Similarity	NPC209944
0.859	High Similarity	NPC241290
0.859	High Similarity	NPC236112
0.859	High Similarity	NPC164840
0.859	High Similarity	NPC234193
0.8571	High Similarity	NPC477522
0.8571	High Similarity	NPC18603
0.8571	High Similarity	NPC6978
0.8571	High Similarity	NPC11908
0.8571	High Similarity	NPC244385
0.8571	High Similarity	NPC473943
0.8571	High Similarity	NPC285761
0.8571	High Similarity	NPC307965
0.8571	High Similarity	NPC76931
0.8571	High Similarity	NPC474216
0.8571	High Similarity	NPC167037
0.8571	High Similarity	NPC138621
0.8571	High Similarity	NPC476314
0.8571	High Similarity	NPC72507
0.8553	High Similarity	NPC96319
0.8553	High Similarity	NPC237460
0.8553	High Similarity	NPC202642
0.8553	High Similarity	NPC470749
0.8553	High Similarity	NPC470362
0.8553	High Similarity	NPC73875
0.8553	High Similarity	NPC46160
0.8553	High Similarity	NPC63958
0.8533	High Similarity	NPC476366
0.8533	High Similarity	NPC201048
0.8533	High Similarity	NPC308440
0.8533	High Similarity	NPC472503
0.8519	High Similarity	NPC470360
0.8514	High Similarity	NPC164022
0.85	High Similarity	NPC113978
0.85	High Similarity	NPC110778
0.85	High Similarity	NPC141941
0.85	High Similarity	NPC193870
0.8493	Intermediate Similarity	NPC210323
0.8481	Intermediate Similarity	NPC116202
0.8481	Intermediate Similarity	NPC264245
0.8481	Intermediate Similarity	NPC47761
0.8472	Intermediate Similarity	NPC269077
0.8472	Intermediate Similarity	NPC253303
0.8462	Intermediate Similarity	NPC84694
0.8462	Intermediate Similarity	NPC109546
0.8462	Intermediate Similarity	NPC30986
0.8462	Intermediate Similarity	NPC209430
0.8462	Intermediate Similarity	NPC80530
0.8462	Intermediate Similarity	NPC273410
0.8462	Intermediate Similarity	NPC81306
0.8462	Intermediate Similarity	NPC100906
0.8462	Intermediate Similarity	NPC143182
0.8462	Intermediate Similarity	NPC28862
0.8462	Intermediate Similarity	NPC47982
0.8462	Intermediate Similarity	NPC328714
0.8452	Intermediate Similarity	NPC3345
0.8452	Intermediate Similarity	NPC329596
0.8452	Intermediate Similarity	NPC80561
0.8452	Intermediate Similarity	NPC295668
0.8452	Intermediate Similarity	NPC11216
0.8452	Intermediate Similarity	NPC291484
0.8452	Intermediate Similarity	NPC204188
0.8442	Intermediate Similarity	NPC34019
0.8434	Intermediate Similarity	NPC470542
0.8434	Intermediate Similarity	NPC133588
0.8421	Intermediate Similarity	NPC322353
0.8421	Intermediate Similarity	NPC118508
0.8421	Intermediate Similarity	NPC103822
0.8421	Intermediate Similarity	NPC121744
0.8415	Intermediate Similarity	NPC299068
0.8395	Intermediate Similarity	NPC205845
0.8395	Intermediate Similarity	NPC470077
0.8395	Intermediate Similarity	NPC238992
0.8378	Intermediate Similarity	NPC34834
0.8375	Intermediate Similarity	NPC470049
0.8375	Intermediate Similarity	NPC304285
0.8375	Intermediate Similarity	NPC101462
0.8375	Intermediate Similarity	NPC296701

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 NPC471798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1609
0.2-0.3	4103
0.3-0.4	2262
0.4-0.5	600
0.5-0.6	204
0.6-0.7	151
0.7-0.8	53
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
0.8701	High Similarity	NPD7645	Phase 2
0.8667	High Similarity	NPD6942	Approved
0.8667	High Similarity	NPD7339	Approved
0.8553	High Similarity	NPD3701	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7525	Registered
0.7952	Intermediate Similarity	NPD4786	Approved
0.7949	Intermediate Similarity	NPD8264	Approved
0.7927	Intermediate Similarity	NPD3667	Approved
0.7882	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4784	Approved
0.7821	Intermediate Similarity	NPD6926	Approved
0.7821	Intermediate Similarity	NPD6924	Approved
0.7821	Intermediate Similarity	NPD4785	Approved
0.7792	Intermediate Similarity	NPD7150	Approved
0.7792	Intermediate Similarity	NPD7152	Approved
0.7792	Intermediate Similarity	NPD7151	Approved
0.7778	Intermediate Similarity	NPD6929	Approved
0.7765	Intermediate Similarity	NPD3618	Phase 1
0.775	Intermediate Similarity	NPD6932	Approved
0.7727	Intermediate Similarity	NPD6079	Approved
0.7701	Intermediate Similarity	NPD5328	Approved
0.7683	Intermediate Similarity	NPD6931	Approved
0.7683	Intermediate Similarity	NPD6930	Phase 2
0.7662	Intermediate Similarity	NPD7143	Approved
0.7662	Intermediate Similarity	NPD7144	Approved
0.7654	Intermediate Similarity	NPD7145	Approved
0.7625	Intermediate Similarity	NPD6933	Approved
0.7564	Intermediate Similarity	NPD4243	Approved
0.7532	Intermediate Similarity	NPD6923	Approved
0.7532	Intermediate Similarity	NPD6922	Approved
0.7531	Intermediate Similarity	NPD5776	Phase 2
0.7531	Intermediate Similarity	NPD6925	Approved
0.7528	Intermediate Similarity	NPD7515	Phase 2
0.747	Intermediate Similarity	NPD7509	Discontinued
0.747	Intermediate Similarity	NPD7514	Phase 3
0.747	Intermediate Similarity	NPD7332	Phase 2
0.747	Intermediate Similarity	NPD4748	Discontinued
0.7412	Intermediate Similarity	NPD6695	Phase 3
0.7381	Intermediate Similarity	NPD6902	Approved
0.7349	Intermediate Similarity	NPD6683	Phase 2
0.7326	Intermediate Similarity	NPD3665	Phase 1
0.7326	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3133	Approved
0.7326	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD4202	Approved
0.7241	Intermediate Similarity	NPD6893	Approved
0.7234	Intermediate Similarity	NPD7638	Approved
0.7229	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5221	Approved
0.7204	Intermediate Similarity	NPD5222	Approved
0.7204	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6898	Phase 1
0.7174	Intermediate Similarity	NPD7748	Approved
0.7158	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7128	Intermediate Similarity	NPD5173	Approved
0.7126	Intermediate Similarity	NPD3668	Phase 3
0.7079	Intermediate Similarity	NPD7750	Discontinued
0.7079	Intermediate Similarity	NPD7524	Approved
0.7073	Intermediate Similarity	NPD4190	Phase 3
0.7073	Intermediate Similarity	NPD5275	Approved
0.7065	Intermediate Similarity	NPD6399	Phase 3
0.7053	Intermediate Similarity	NPD5290	Discontinued
0.7045	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4697	Phase 3
0.6979	Remote Similarity	NPD5285	Approved
0.6979	Remote Similarity	NPD5286	Approved
0.6979	Remote Similarity	NPD4696	Approved
0.6947	Remote Similarity	NPD4755	Approved
0.6947	Remote Similarity	NPD7902	Approved
0.6907	Remote Similarity	NPD5223	Approved
0.686	Remote Similarity	NPD4695	Discontinued
0.6842	Remote Similarity	NPD368	Approved
0.6837	Remote Similarity	NPD5226	Approved
0.6837	Remote Similarity	NPD4633	Approved
0.6837	Remote Similarity	NPD5211	Phase 2
0.6837	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD5225	Approved
0.6804	Remote Similarity	NPD4700	Approved
0.6778	Remote Similarity	NPD5279	Phase 3
0.6774	Remote Similarity	NPD6411	Approved
0.6774	Remote Similarity	NPD7087	Discontinued
0.6768	Remote Similarity	NPD5174	Approved
0.6768	Remote Similarity	NPD5175	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6705	Remote Similarity	NPD4221	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.67	Remote Similarity	NPD5141	Approved
0.6699	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD7136	Phase 2
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6634	Remote Similarity	NPD5739	Approved
0.6634	Remote Similarity	NPD6675	Approved
0.6634	Remote Similarity	NPD6402	Approved
0.6634	Remote Similarity	NPD7128	Approved
0.6632	Remote Similarity	NPD7900	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4754	Approved
0.6596	Remote Similarity	NPD7637	Suspended
0.6593	Remote Similarity	NPD7334	Approved
0.6593	Remote Similarity	NPD4623	Approved
0.6593	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7521	Approved
0.6593	Remote Similarity	NPD5330	Approved
0.6593	Remote Similarity	NPD6409	Approved
0.6593	Remote Similarity	NPD7146	Approved
0.6593	Remote Similarity	NPD6684	Approved
0.6593	Remote Similarity	NPD4519	Discontinued
0.6569	Remote Similarity	NPD5697	Approved
0.6562	Remote Similarity	NPD4629	Approved
0.6562	Remote Similarity	NPD5210	Approved
0.6559	Remote Similarity	NPD6101	Approved
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4197	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6538	Remote Similarity	NPD7102	Approved
0.6531	Remote Similarity	NPD4225	Approved
0.6526	Remote Similarity	NPD5778	Approved
0.6526	Remote Similarity	NPD5779	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6509	Remote Similarity	NPD4632	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD4729	Approved
0.6505	Remote Similarity	NPD5168	Approved
0.6505	Remote Similarity	NPD4730	Approved
0.6505	Remote Similarity	NPD7320	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6486	Remote Similarity	NPD342	Phase 1
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD6617	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD8130	Phase 1
0.6471	Remote Similarity	NPD3703	Phase 2
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6452	Remote Similarity	NPD6903	Approved
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4788	Approved
0.6442	Remote Similarity	NPD6373	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6372	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD6697	Approved
0.6437	Remote Similarity	NPD6115	Approved
0.6437	Remote Similarity	NPD6118	Approved
0.6437	Remote Similarity	NPD6114	Approved
0.6437	Remote Similarity	NPD3617	Approved
0.6429	Remote Similarity	NPD4732	Discontinued
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6421	Remote Similarity	NPD8035	Phase 2
0.6421	Remote Similarity	NPD8034	Phase 2
0.6415	Remote Similarity	NPD8297	Approved
0.6415	Remote Similarity	NPD6882	Approved
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD4688	Approved
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD5690	Phase 2
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD4689	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.6408	Remote Similarity	NPD5701	Approved
0.64	Remote Similarity	NPD4159	Approved
0.6386	Remote Similarity	NPD4787	Phase 1
0.6383	Remote Similarity	NPD6051	Approved
0.6383	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5249	Phase 3
0.6381	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5247	Approved
0.6381	Remote Similarity	NPD5248	Approved
0.6381	Remote Similarity	NPD5135	Approved
0.6381	Remote Similarity	NPD5250	Approved
0.6381	Remote Similarity	NPD5251	Approved
0.6381	Remote Similarity	NPD5169	Approved
0.6346	Remote Similarity	NPD5128	Approved
0.633	Remote Similarity	NPD7115	Discovery
0.633	Remote Similarity	NPD6009	Approved
0.6321	Remote Similarity	NPD5216	Approved
0.6321	Remote Similarity	NPD5127	Approved
0.6321	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5215	Approved
0.6321	Remote Similarity	NPD5217	Approved
0.6311	Remote Similarity	NPD6008	Approved
0.631	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6054	Approved
0.6286	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4722	Approved
0.6277	Remote Similarity	NPD6672	Approved
0.6277	Remote Similarity	NPD4723	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