NPASS Compound

Structure

NPC471794 OpenBabel07101718312D 22 24 0 0 1 0 0 0 0 0999 V2000 -6.0032 2.9483 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 -4.1996 3.4914 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 -5.2961 2.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 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 2.5000 0.0000 C 0 0 1 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 -4.3301 -0.5000 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 11 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 6 0 0 0 15 20 1 6 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.19
Volume:	327.336
LogP:	3.666
LogD:	2.711
LogS:	-3.672
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	4.455
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.8
MDCK Permeability:	2.3005777620710433e-05
Pgp-inhibitor:	0.336
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.722

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	98.57060241699219%
Volume Distribution (VD):	0.89
Pgp-substrate:	3.611241340637207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.844
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.705
CYP2C9-inhibitor:	0.176
CYP2C9-substrate:	0.65
CYP2D6-inhibitor:	0.464
CYP2D6-substrate:	0.476
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	3.017
Half-life (T1/2):	0.682

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.414
Skin Sensitization:	0.945
Carcinogencity:	0.091
Eye Corrosion:	0.214
Eye Irritation:	0.946
Respiratory Toxicity:	0.586

Download Data

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

Natural Product: NPC471794

Natural Product ID:	NPC471794
*Common Name:**	Ebractenoid G
IUPAC Name:	(4bR,7R,8aR,9S)-7-ethenyl-1,4b,7-trimethyl-5,6,8,8a,9,10-hexahydrophenanthrene-2,3,9-triol
Synonyms:
Standard InCHIKey:	WRBYHCXJVBWVFG-SAKMYQHLSA-N
Standard InCHI:	InChI=1S/C19H26O3/c1-5-18(3)6-7-19(4)13-9-16(21)17(22)11(2)12(13)8-15(20)14(19)10-18/h5,9,14-15,20-22H,1,6-8,10H2,2-4H3/t14-,15-,18+,19-/m0/s1
SMILES:	C=C[C@]1(C)CC[C@@]2([C@@H](C1)[C@@H](O)Cc1c2cc(O)c(c1C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234211
PubChem CID:	90670334
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	=	2440.0	nM	PMID[536119]

☑ 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 NPC471794 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	332
0.1-0.2	1426
0.2-0.3	3371
0.3-0.4	9032
0.4-0.5	10538
0.5-0.6	8219
0.6-0.7	7454
0.7-0.8	2135
0.8-0.85	133
0.85-0.9	37
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC16030
0.9397	High Similarity	NPC469609
0.9304	High Similarity	NPC147179
0.9231	High Similarity	NPC471671
0.9224	High Similarity	NPC219112
0.9224	High Similarity	NPC308828
0.9217	High Similarity	NPC268160
0.9153	High Similarity	NPC469644
0.9145	High Similarity	NPC304510
0.9145	High Similarity	NPC172219
0.9106	High Similarity	NPC476536
0.906	High Similarity	NPC38893
0.906	High Similarity	NPC477137
0.906	High Similarity	NPC308311
0.9008	High Similarity	NPC321402
0.8983	High Similarity	NPC477136
0.8974	High Similarity	NPC192948
0.8974	High Similarity	NPC35797
0.8968	High Similarity	NPC312341
0.8952	High Similarity	NPC471077
0.8908	High Similarity	NPC154030
0.8898	High Similarity	NPC469663
0.8898	High Similarity	NPC92
0.887	High Similarity	NPC141782
0.8843	High Similarity	NPC328504
0.8833	High Similarity	NPC176893
0.8828	High Similarity	NPC227719
0.8803	High Similarity	NPC317869
0.879	High Similarity	NPC87985
0.877	High Similarity	NPC142198
0.877	High Similarity	NPC77569
0.876	High Similarity	NPC260832
0.876	High Similarity	NPC135467
0.875	High Similarity	NPC59239
0.874	High Similarity	NPC99795
0.8729	High Similarity	NPC120280
0.8718	High Similarity	NPC228425
0.8718	High Similarity	NPC471179
0.8672	High Similarity	NPC78575
0.8632	High Similarity	NPC260323
0.8632	High Similarity	NPC176279
0.8629	High Similarity	NPC53567
0.8626	High Similarity	NPC68292
0.8618	High Similarity	NPC475166
0.8607	High Similarity	NPC475245
0.8595	High Similarity	NPC164649
0.8595	High Similarity	NPC48342
0.8571	High Similarity	NPC195922
0.8571	High Similarity	NPC471534
0.856	High Similarity	NPC224342
0.8559	High Similarity	NPC250323
0.855	High Similarity	NPC103082
0.8547	High Similarity	NPC13482
0.8487	Intermediate Similarity	NPC471485
0.848	Intermediate Similarity	NPC198014
0.8475	Intermediate Similarity	NPC95716
0.8468	Intermediate Similarity	NPC237667
0.8468	Intermediate Similarity	NPC474115
0.8468	Intermediate Similarity	NPC253627
0.8462	Intermediate Similarity	NPC55617
0.8462	Intermediate Similarity	NPC62258
0.8455	Intermediate Similarity	NPC68339
0.8438	Intermediate Similarity	NPC201069
0.843	Intermediate Similarity	NPC471668
0.843	Intermediate Similarity	NPC474387
0.843	Intermediate Similarity	NPC154511
0.843	Intermediate Similarity	NPC247858
0.843	Intermediate Similarity	NPC474358
0.843	Intermediate Similarity	NPC257540
0.843	Intermediate Similarity	NPC141001
0.843	Intermediate Similarity	NPC137496
0.8425	Intermediate Similarity	NPC321822
0.8425	Intermediate Similarity	NPC325294
0.8417	Intermediate Similarity	NPC12656
0.8413	Intermediate Similarity	NPC181334
0.8403	Intermediate Similarity	NPC46940
0.84	Intermediate Similarity	NPC71094
0.8397	Intermediate Similarity	NPC474453
0.839	Intermediate Similarity	NPC120982
0.839	Intermediate Similarity	NPC132720
0.839	Intermediate Similarity	NPC79793
0.839	Intermediate Similarity	NPC174096
0.839	Intermediate Similarity	NPC226401
0.839	Intermediate Similarity	NPC147634
0.8385	Intermediate Similarity	NPC291001
0.8376	Intermediate Similarity	NPC149455
0.8376	Intermediate Similarity	NPC11554
0.8376	Intermediate Similarity	NPC64642
0.8376	Intermediate Similarity	NPC472982
0.8362	Intermediate Similarity	NPC477814
0.8347	Intermediate Similarity	NPC474486
0.8346	Intermediate Similarity	NPC124030
0.8333	Intermediate Similarity	NPC311256
0.8333	Intermediate Similarity	NPC715
0.8333	Intermediate Similarity	NPC471187
0.8321	Intermediate Similarity	NPC321502
0.8319	Intermediate Similarity	NPC187583
0.8319	Intermediate Similarity	NPC322753
0.8319	Intermediate Similarity	NPC179002
0.8319	Intermediate Similarity	NPC257430
0.8319	Intermediate Similarity	NPC77772
0.8319	Intermediate Similarity	NPC151537
0.8306	Intermediate Similarity	NPC472071
0.8305	Intermediate Similarity	NPC228343
0.8305	Intermediate Similarity	NPC254833
0.8295	Intermediate Similarity	NPC307050
0.8295	Intermediate Similarity	NPC277458
0.8291	Intermediate Similarity	NPC151477
0.8281	Intermediate Similarity	NPC100414
0.8281	Intermediate Similarity	NPC470724
0.8281	Intermediate Similarity	NPC43000
0.8268	Intermediate Similarity	NPC15127
0.8264	Intermediate Similarity	NPC473137
0.8258	Intermediate Similarity	NPC476282
0.8254	Intermediate Similarity	NPC11250
0.8254	Intermediate Similarity	NPC152946
0.8248	Intermediate Similarity	NPC248068
0.8244	Intermediate Similarity	NPC243305
0.824	Intermediate Similarity	NPC24125
0.8235	Intermediate Similarity	NPC44732
0.8235	Intermediate Similarity	NPC471853
0.8231	Intermediate Similarity	NPC470747
0.8226	Intermediate Similarity	NPC93071
0.8226	Intermediate Similarity	NPC151197
0.8226	Intermediate Similarity	NPC217174
0.8226	Intermediate Similarity	NPC191866
0.8226	Intermediate Similarity	NPC126002
0.8222	Intermediate Similarity	NPC184613
0.822	Intermediate Similarity	NPC233835
0.8217	Intermediate Similarity	NPC108164
0.8217	Intermediate Similarity	NPC186889
0.8211	Intermediate Similarity	NPC277588
0.8209	Intermediate Similarity	NPC470733
0.8203	Intermediate Similarity	NPC76119
0.8203	Intermediate Similarity	NPC29008
0.8203	Intermediate Similarity	NPC228771
0.8203	Intermediate Similarity	NPC4286
0.8203	Intermediate Similarity	NPC266705
0.8197	Intermediate Similarity	NPC469719
0.8195	Intermediate Similarity	NPC293454
0.8195	Intermediate Similarity	NPC471942
0.819	Intermediate Similarity	NPC120719
0.819	Intermediate Similarity	NPC12278
0.8182	Intermediate Similarity	NPC303144
0.8182	Intermediate Similarity	NPC228843
0.8175	Intermediate Similarity	NPC39029
0.8168	Intermediate Similarity	NPC143483
0.8167	Intermediate Similarity	NPC308689
0.8167	Intermediate Similarity	NPC266937
0.8167	Intermediate Similarity	NPC470770
0.816	Intermediate Similarity	NPC223451
0.8151	Intermediate Similarity	NPC58865
0.8145	Intermediate Similarity	NPC206
0.8145	Intermediate Similarity	NPC144343
0.814	Intermediate Similarity	NPC71610
0.8136	Intermediate Similarity	NPC27252
0.8136	Intermediate Similarity	NPC472979
0.8134	Intermediate Similarity	NPC313081
0.8134	Intermediate Similarity	NPC241241
0.8129	Intermediate Similarity	NPC126707
0.812	Intermediate Similarity	NPC243601
0.812	Intermediate Similarity	NPC239291
0.812	Intermediate Similarity	NPC117115
0.8115	Intermediate Similarity	NPC107240
0.811	Intermediate Similarity	NPC478058
0.8106	Intermediate Similarity	NPC476847
0.8099	Intermediate Similarity	NPC473521
0.8099	Intermediate Similarity	NPC62867
0.8099	Intermediate Similarity	NPC177962
0.8095	Intermediate Similarity	NPC259703
0.8095	Intermediate Similarity	NPC470414
0.8095	Intermediate Similarity	NPC32322
0.8088	Intermediate Similarity	NPC6300
0.8088	Intermediate Similarity	NPC182249
0.8088	Intermediate Similarity	NPC230124
0.8088	Intermediate Similarity	NPC114171
0.8088	Intermediate Similarity	NPC474640
0.8088	Intermediate Similarity	NPC475757
0.808	Intermediate Similarity	NPC323074
0.8074	Intermediate Similarity	NPC30632
0.8067	Intermediate Similarity	NPC262365
0.8065	Intermediate Similarity	NPC320864
0.8062	Intermediate Similarity	NPC137750
0.8062	Intermediate Similarity	NPC148627
0.8062	Intermediate Similarity	NPC470726
0.8062	Intermediate Similarity	NPC9067
0.8058	Intermediate Similarity	NPC473845
0.8051	Intermediate Similarity	NPC271274
0.8051	Intermediate Similarity	NPC21594
0.8049	Intermediate Similarity	NPC246760
0.8049	Intermediate Similarity	NPC84999
0.8047	Intermediate Similarity	NPC473451
0.8045	Intermediate Similarity	NPC321086
0.8043	Intermediate Similarity	NPC2681
0.8043	Intermediate Similarity	NPC272907
0.8031	Intermediate Similarity	NPC249340
0.8031	Intermediate Similarity	NPC162935
0.803	Intermediate Similarity	NPC470727
0.803	Intermediate Similarity	NPC196193
0.8029	Intermediate Similarity	NPC155192

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 NPC471794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	840
0.2-0.3	1591
0.3-0.4	2956
0.4-0.5	1865
0.5-0.6	1101
0.6-0.7	398
0.7-0.8	86
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.877	High Similarity	NPD3092	Approved
0.8595	High Similarity	NPD3091	Approved
0.8492	Intermediate Similarity	NPD3094	Phase 2
0.8321	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3620	Phase 2
0.8305	Intermediate Similarity	NPD3022	Approved
0.8305	Intermediate Similarity	NPD3021	Approved
0.816	Intermediate Similarity	NPD3095	Discontinued
0.7874	Intermediate Similarity	NPD4059	Approved
0.7874	Intermediate Similarity	NPD3019	Approved
0.7833	Intermediate Similarity	NPD2342	Discontinued
0.7817	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7635	Approved
0.7803	Intermediate Similarity	NPD5736	Approved
0.7734	Intermediate Similarity	NPD2932	Approved
0.7721	Intermediate Similarity	NPD5735	Approved
0.7692	Intermediate Similarity	NPD3020	Approved
0.76	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1809	Phase 2
0.7574	Intermediate Similarity	NPD6663	Approved
0.7571	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3645	Discontinued
0.7569	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4750	Phase 3
0.7556	Intermediate Similarity	NPD3027	Phase 3
0.7535	Intermediate Similarity	NPD8166	Discontinued
0.7521	Intermediate Similarity	NPD288	Approved
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2859	Approved
0.7436	Intermediate Similarity	NPD844	Approved
0.7436	Intermediate Similarity	NPD2860	Approved
0.7429	Intermediate Similarity	NPD7742	Approved
0.7429	Intermediate Similarity	NPD7743	Approved
0.7414	Intermediate Similarity	NPD845	Approved
0.741	Intermediate Similarity	NPD4097	Suspended
0.7391	Intermediate Similarity	NPD4140	Approved
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4060	Phase 1
0.7391	Intermediate Similarity	NPD1613	Approved
0.7385	Intermediate Similarity	NPD4093	Discontinued
0.7368	Intermediate Similarity	NPD5327	Phase 3
0.735	Intermediate Similarity	NPD2933	Approved
0.735	Intermediate Similarity	NPD2934	Approved
0.7348	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6674	Discontinued
0.7343	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4624	Approved
0.7333	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1751	Approved
0.7328	Intermediate Similarity	NPD9381	Approved
0.7328	Intermediate Similarity	NPD9384	Approved
0.7328	Intermediate Similarity	NPD2286	Discontinued
0.7323	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD228	Approved
0.7302	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2861	Phase 2
0.7273	Intermediate Similarity	NPD3026	Approved
0.7273	Intermediate Similarity	NPD846	Approved
0.7273	Intermediate Similarity	NPD940	Approved
0.7273	Intermediate Similarity	NPD3023	Approved
0.726	Intermediate Similarity	NPD2420	Approved
0.726	Intermediate Similarity	NPD2421	Approved
0.7252	Intermediate Similarity	NPD3025	Approved
0.7252	Intermediate Similarity	NPD3024	Approved
0.7246	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD9622	Approved
0.7226	Intermediate Similarity	NPD2605	Approved
0.7226	Intermediate Similarity	NPD2606	Approved
0.7222	Intermediate Similarity	NPD3638	Discontinued
0.7218	Intermediate Similarity	NPD1201	Approved
0.7214	Intermediate Similarity	NPD3657	Discovery
0.7213	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4626	Approved
0.7197	Intermediate Similarity	NPD2489	Approved
0.7197	Intermediate Similarity	NPD27	Approved
0.7188	Intermediate Similarity	NPD5283	Phase 1
0.7185	Intermediate Similarity	NPD6696	Suspended
0.7185	Intermediate Similarity	NPD8651	Approved
0.7174	Intermediate Similarity	NPD5156	Approved
0.7174	Intermediate Similarity	NPD5155	Approved
0.7174	Intermediate Similarity	NPD4625	Phase 3
0.7163	Intermediate Similarity	NPD6353	Approved
0.7153	Intermediate Similarity	NPD3636	Approved
0.7153	Intermediate Similarity	NPD3637	Approved
0.7153	Intermediate Similarity	NPD3635	Approved
0.7143	Intermediate Similarity	NPD3062	Approved
0.7143	Intermediate Similarity	NPD3061	Approved
0.7143	Intermediate Similarity	NPD3059	Approved
0.7132	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3595	Approved
0.7101	Intermediate Similarity	NPD4908	Phase 1
0.7101	Intermediate Similarity	NPD3594	Approved
0.7083	Intermediate Similarity	NPD7266	Discontinued
0.7083	Intermediate Similarity	NPD4726	Approved
0.7083	Intermediate Similarity	NPD5762	Approved
0.7083	Intermediate Similarity	NPD4725	Approved
0.7083	Intermediate Similarity	NPD4721	Approved
0.7083	Intermediate Similarity	NPD5763	Approved
0.708	Intermediate Similarity	NPD9620	Approved
0.708	Intermediate Similarity	NPD2195	Approved
0.708	Intermediate Similarity	NPD9619	Approved
0.708	Intermediate Similarity	NPD9621	Approved
0.708	Intermediate Similarity	NPD2194	Approved
0.707	Intermediate Similarity	NPD3051	Approved
0.7068	Intermediate Similarity	NPD4589	Approved
0.7049	Intermediate Similarity	NPD1242	Phase 1
0.7045	Intermediate Similarity	NPD7741	Discontinued
0.7042	Intermediate Similarity	NPD5314	Approved
0.7029	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2970	Approved
0.7025	Intermediate Similarity	NPD2969	Approved
0.7023	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1792	Phase 2
0.7007	Intermediate Similarity	NPD1470	Approved
0.7	Intermediate Similarity	NPD598	Approved
0.7	Intermediate Similarity	NPD597	Approved
0.7	Intermediate Similarity	NPD601	Approved
0.6993	Remote Similarity	NPD37	Approved
0.6992	Remote Similarity	NPD1357	Approved
0.6992	Remote Similarity	NPD5691	Approved
0.6987	Remote Similarity	NPD6234	Discontinued
0.6985	Remote Similarity	NPD4659	Approved
0.6977	Remote Similarity	NPD9379	Approved
0.6977	Remote Similarity	NPD9377	Approved
0.6963	Remote Similarity	NPD1610	Phase 2
0.6953	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1136	Approved
0.695	Remote Similarity	NPD1132	Approved
0.695	Remote Similarity	NPD1130	Approved
0.6947	Remote Similarity	NPD7157	Approved
0.6923	Remote Similarity	NPD817	Approved
0.6923	Remote Similarity	NPD2228	Approved
0.6923	Remote Similarity	NPD2229	Approved
0.6923	Remote Similarity	NPD823	Approved
0.6923	Remote Similarity	NPD2234	Approved
0.6917	Remote Similarity	NPD5303	Approved
0.6917	Remote Similarity	NPD5304	Approved
0.6913	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7041	Phase 2
0.6901	Remote Similarity	NPD2238	Phase 2
0.6897	Remote Similarity	NPD5404	Approved
0.6897	Remote Similarity	NPD5406	Approved
0.6897	Remote Similarity	NPD5408	Approved
0.6897	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5405	Approved
0.6884	Remote Similarity	NPD4103	Phase 2
0.6884	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3053	Approved
0.6884	Remote Similarity	NPD3055	Approved
0.687	Remote Similarity	NPD497	Approved
0.6861	Remote Similarity	NPD4749	Approved
0.6861	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4967	Phase 2
0.6859	Remote Similarity	NPD4966	Approved
0.6859	Remote Similarity	NPD4965	Approved
0.6846	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3845	Phase 1
0.6839	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6405	Approved
0.6831	Remote Similarity	NPD6407	Approved
0.6828	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7003	Approved
0.6815	Remote Similarity	NPD5125	Phase 3
0.6815	Remote Similarity	NPD5126	Approved
0.6812	Remote Similarity	NPD5311	Approved
0.6812	Remote Similarity	NPD5310	Approved
0.6812	Remote Similarity	NPD1283	Approved
0.6797	Remote Similarity	NPD2684	Approved
0.6794	Remote Similarity	NPD496	Approved
0.6794	Remote Similarity	NPD498	Approved
0.6794	Remote Similarity	NPD495	Approved
0.6792	Remote Similarity	NPD8127	Discontinued
0.6791	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7228	Approved
0.6783	Remote Similarity	NPD943	Approved
0.6779	Remote Similarity	NPD6190	Approved
0.6779	Remote Similarity	NPD5241	Discontinued
0.6772	Remote Similarity	NPD1444	Approved
0.6772	Remote Similarity	NPD1445	Approved
0.6767	Remote Similarity	NPD7340	Approved
0.6763	Remote Similarity	NPD1134	Approved
0.6763	Remote Similarity	NPD1133	Approved
0.6763	Remote Similarity	NPD1135	Approved
0.6763	Remote Similarity	NPD1131	Approved
0.6763	Remote Similarity	NPD1129	Approved
0.6747	Remote Similarity	NPD4577	Approved
0.6747	Remote Similarity	NPD4578	Approved
0.6744	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2629	Approved
0.6741	Remote Similarity	NPD1651	Approved
0.6726	Remote Similarity	NPD4663	Approved
0.6724	Remote Similarity	NPD111	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