NPASS Compound

Structure

NPC72915 OpenBabel07101719152D 25 28 0 0 1 0 0 0 0 0999 V2000 -1.6942 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3703 0.7698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2456 -0.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2675 -0.9694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5546 0.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5983 -0.2262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8855 0.9328 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 0.8660 -1.0860 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 0.1715 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 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 -2.9074 0.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5605 -0.7515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3424 -1.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 6 0 0 0 17 21 1 6 0 0 0 17 23 1 0 0 0 0 18 22 1 6 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 21 3 1 1 0 0 0 22 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.22
Volume:	370.667
LogP:	4.484
LogD:	4.22
LogS:	-4.782
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	5.169
Fsp3:	0.682
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:	-4.861
MDCK Permeability:	2.47041170950979e-05
Pgp-inhibitor:	0.488
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.16
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	97.93566131591797%
Volume Distribution (VD):	1.032
Pgp-substrate:	3.64412522315979%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.157
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.795
CYP2C9-inhibitor:	0.336
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.197
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	8.62
Half-life (T1/2):	0.206

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.799
Skin Sensitization:	0.687
Carcinogencity:	0.052
Eye Corrosion:	0.035
Eye Irritation:	0.608
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC72915

Natural Product ID:	NPC72915
*Common Name:**	Canangaterpene Ii
IUPAC Name:	[(3S,3aR,6R,7S,9aR)-6-hydroxy-1,1,7-trimethyl-3,4,5,6,8,9,9a,10-octahydro-2H-tricyclo[6.3.1.0^{1,5}]dodecan-3-yl] benzoate
Synonyms:
Standard InCHIKey:	HDIDNZWPPAQDGI-XPMXXILHSA-N
Standard InCHI:	InChI=1S/C22H30O3/c1-20(2)13-18(25-19(24)15-7-5-4-6-8-15)22-12-10-17(23)21(3,14-22)11-9-16(20)22/h4-8,16-18,23H,9-14H2,1-3H3/t16-,17-,18+,21+,22-/m1/s1
SMILES:	O[C@@H]1CC[C@]23C[C@]1(C)CC[C@@H]3C(C[C@@H]2OC(=O)c1ccccc1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3262197
PubChem CID:	90676283
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11374955]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	flower buds	Thailand	n.a.	PMID[24601675]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9348	Cananga odorata	Species	Annonaceae	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
Others	5

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	45.3	%	PMID[479538]
NPT2	Others	Unspecified	Inhibition	=	40.2	%	PMID[479538]
NPT2	Others	Unspecified	Inhibition	=	66.7	%	PMID[479538]
NPT27	Others	Unspecified	Activity	=	7.9	%	PMID[479538]
NPT27	Others	Unspecified	Activity	=	75.9	%	PMID[479538]
NPT2	Others	Unspecified	IC50	=	3000.0	nM	PMID[479538]

☑ 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 NPC72915 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	253
0.1-0.2	1050
0.2-0.3	2017
0.3-0.4	4180
0.4-0.5	8593
0.5-0.6	15653
0.6-0.7	9222
0.7-0.8	1393
0.8-0.85	223
0.85-0.9	110
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9302	High Similarity	NPC48929
0.9008	High Similarity	NPC203486
0.8864	High Similarity	NPC126516
0.8846	High Similarity	NPC82712
0.8828	High Similarity	NPC275576
0.876	High Similarity	NPC473220
0.876	High Similarity	NPC169913
0.876	High Similarity	NPC470753
0.8722	High Similarity	NPC329913
0.8705	High Similarity	NPC478263
0.8702	High Similarity	NPC147561
0.8682	High Similarity	NPC470765
0.8676	High Similarity	NPC100913
0.8676	High Similarity	NPC90614
0.8676	High Similarity	NPC275592
0.8667	High Similarity	NPC39549
0.8657	High Similarity	NPC477893
0.8652	High Similarity	NPC476173
0.8636	High Similarity	NPC470278
0.8633	High Similarity	NPC478264
0.8615	High Similarity	NPC472706
0.8613	High Similarity	NPC27377
0.8613	High Similarity	NPC97947
0.8613	High Similarity	NPC41481
0.8613	High Similarity	NPC87448
0.8613	High Similarity	NPC472576
0.8613	High Similarity	NPC291599
0.8613	High Similarity	NPC118080
0.8593	High Similarity	NPC472372
0.8593	High Similarity	NPC472551
0.8593	High Similarity	NPC472545
0.8593	High Similarity	NPC472374
0.8571	High Similarity	NPC473602
0.8571	High Similarity	NPC233692
0.8571	High Similarity	NPC239358
0.8551	High Similarity	NPC475135
0.854	High Similarity	NPC171207
0.854	High Similarity	NPC472547
0.854	High Similarity	NPC97667
0.8529	High Similarity	NPC475373
0.8519	High Similarity	NPC477896
0.8507	High Similarity	NPC472248
0.8489	Intermediate Similarity	NPC163087
0.8489	Intermediate Similarity	NPC91703
0.8478	Intermediate Similarity	NPC266374
0.8478	Intermediate Similarity	NPC224491
0.8478	Intermediate Similarity	NPC16912
0.8467	Intermediate Similarity	NPC9905
0.8467	Intermediate Similarity	NPC473301
0.8462	Intermediate Similarity	NPC279442
0.8451	Intermediate Similarity	NPC76103
0.8444	Intermediate Similarity	NPC28836
0.8444	Intermediate Similarity	NPC474608
0.8444	Intermediate Similarity	NPC311492
0.844	Intermediate Similarity	NPC312393
0.8433	Intermediate Similarity	NPC233860
0.8429	Intermediate Similarity	NPC475122
0.8429	Intermediate Similarity	NPC475759
0.8429	Intermediate Similarity	NPC470152
0.8429	Intermediate Similarity	NPC241951
0.8417	Intermediate Similarity	NPC192658
0.8406	Intermediate Similarity	NPC87934
0.8406	Intermediate Similarity	NPC162613
0.8394	Intermediate Similarity	NPC262324
0.8392	Intermediate Similarity	NPC125033
0.8382	Intermediate Similarity	NPC472577
0.8382	Intermediate Similarity	NPC200154
0.8382	Intermediate Similarity	NPC17877
0.8382	Intermediate Similarity	NPC195647
0.8382	Intermediate Similarity	NPC291638
0.8382	Intermediate Similarity	NPC471864
0.8382	Intermediate Similarity	NPC66761
0.838	Intermediate Similarity	NPC473760
0.838	Intermediate Similarity	NPC327031
0.837	Intermediate Similarity	NPC472656
0.8369	Intermediate Similarity	NPC158663
0.8369	Intermediate Similarity	NPC472572
0.8369	Intermediate Similarity	NPC472571
0.8369	Intermediate Similarity	NPC476973
0.8369	Intermediate Similarity	NPC472575
0.8369	Intermediate Similarity	NPC171525
0.8369	Intermediate Similarity	NPC470159
0.8369	Intermediate Similarity	NPC70403
0.8369	Intermediate Similarity	NPC471104
0.8369	Intermediate Similarity	NPC472568
0.8369	Intermediate Similarity	NPC29704
0.8369	Intermediate Similarity	NPC200471
0.8369	Intermediate Similarity	NPC177940
0.8369	Intermediate Similarity	NPC470157
0.8369	Intermediate Similarity	NPC472556
0.8369	Intermediate Similarity	NPC96903
0.8369	Intermediate Similarity	NPC473088
0.8369	Intermediate Similarity	NPC184817
0.8369	Intermediate Similarity	NPC469349
0.8369	Intermediate Similarity	NPC174982
0.8367	Intermediate Similarity	NPC476784
0.8357	Intermediate Similarity	NPC477894
0.8357	Intermediate Similarity	NPC191387
0.8357	Intermediate Similarity	NPC131966
0.8345	Intermediate Similarity	NPC472658
0.8345	Intermediate Similarity	NPC472657
0.8345	Intermediate Similarity	NPC242355
0.8333	Intermediate Similarity	NPC253681
0.8333	Intermediate Similarity	NPC96308
0.8321	Intermediate Similarity	NPC202729
0.831	Intermediate Similarity	NPC209592
0.831	Intermediate Similarity	NPC48599
0.8308	Intermediate Similarity	NPC472703
0.8306	Intermediate Similarity	NPC128368
0.8298	Intermediate Similarity	NPC25768
0.8298	Intermediate Similarity	NPC95810
0.8298	Intermediate Similarity	NPC188865
0.8298	Intermediate Similarity	NPC472569
0.8298	Intermediate Similarity	NPC95265
0.8298	Intermediate Similarity	NPC472573
0.8298	Intermediate Similarity	NPC57628
0.8298	Intermediate Similarity	NPC34943
0.8298	Intermediate Similarity	NPC70716
0.8298	Intermediate Similarity	NPC125106
0.8298	Intermediate Similarity	NPC472570
0.8298	Intermediate Similarity	NPC476974
0.8298	Intermediate Similarity	NPC11685
0.8298	Intermediate Similarity	NPC163719
0.8288	Intermediate Similarity	NPC469456
0.8286	Intermediate Similarity	NPC183540
0.8286	Intermediate Similarity	NPC472546
0.8286	Intermediate Similarity	NPC182869
0.8286	Intermediate Similarity	NPC34012
0.8273	Intermediate Similarity	NPC473440
0.8273	Intermediate Similarity	NPC79921
0.8261	Intermediate Similarity	NPC283375
0.8261	Intermediate Similarity	NPC27721
0.8261	Intermediate Similarity	NPC183122
0.8261	Intermediate Similarity	NPC243893
0.8248	Intermediate Similarity	NPC473216
0.8248	Intermediate Similarity	NPC473399
0.8244	Intermediate Similarity	NPC472704
0.8239	Intermediate Similarity	NPC125882
0.8239	Intermediate Similarity	NPC311825
0.8239	Intermediate Similarity	NPC92867
0.8219	Intermediate Similarity	NPC471135
0.8201	Intermediate Similarity	NPC477592
0.8201	Intermediate Similarity	NPC214550
0.8201	Intermediate Similarity	NPC475652
0.8201	Intermediate Similarity	NPC210591
0.8194	Intermediate Similarity	NPC92293
0.8194	Intermediate Similarity	NPC471101
0.8194	Intermediate Similarity	NPC270590
0.8194	Intermediate Similarity	NPC266265
0.8194	Intermediate Similarity	NPC473215
0.8194	Intermediate Similarity	NPC301556
0.8194	Intermediate Similarity	NPC476975
0.8182	Intermediate Similarity	NPC20255
0.8182	Intermediate Similarity	NPC240115
0.8182	Intermediate Similarity	NPC474935
0.8176	Intermediate Similarity	NPC322048
0.8176	Intermediate Similarity	NPC318447
0.8175	Intermediate Similarity	NPC153617
0.8175	Intermediate Similarity	NPC310662
0.8169	Intermediate Similarity	NPC38696
0.8163	Intermediate Similarity	NPC469730
0.8163	Intermediate Similarity	NPC473632
0.8163	Intermediate Similarity	NPC132599
0.8162	Intermediate Similarity	NPC472394
0.8162	Intermediate Similarity	NPC238370
0.8154	Intermediate Similarity	NPC50872
0.8148	Intermediate Similarity	NPC475508
0.8148	Intermediate Similarity	NPC475138
0.8143	Intermediate Similarity	NPC147880
0.8143	Intermediate Similarity	NPC473109
0.8143	Intermediate Similarity	NPC473081
0.8143	Intermediate Similarity	NPC473613
0.8143	Intermediate Similarity	NPC184747
0.8143	Intermediate Similarity	NPC211137
0.8143	Intermediate Similarity	NPC473112
0.8143	Intermediate Similarity	NPC473085
0.8143	Intermediate Similarity	NPC4341
0.8143	Intermediate Similarity	NPC200592
0.8143	Intermediate Similarity	NPC476094
0.8143	Intermediate Similarity	NPC48017
0.8143	Intermediate Similarity	NPC43241
0.8143	Intermediate Similarity	NPC473060
0.8143	Intermediate Similarity	NPC473758
0.8138	Intermediate Similarity	NPC469448
0.8138	Intermediate Similarity	NPC475561
0.8138	Intermediate Similarity	NPC475417
0.8138	Intermediate Similarity	NPC473214
0.8138	Intermediate Similarity	NPC470245
0.8138	Intermediate Similarity	NPC31829
0.8134	Intermediate Similarity	NPC472707
0.8129	Intermediate Similarity	NPC327511
0.8129	Intermediate Similarity	NPC205305
0.8125	Intermediate Similarity	NPC132652
0.8125	Intermediate Similarity	NPC281717
0.8125	Intermediate Similarity	NPC45794
0.8112	Intermediate Similarity	NPC127857
0.8108	Intermediate Similarity	NPC70344
0.8108	Intermediate Similarity	NPC323001
0.8108	Intermediate Similarity	NPC326235
0.8108	Intermediate Similarity	NPC475638

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 NPC72915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	738
0.2-0.3	1261
0.3-0.4	2551
0.4-0.5	2489
0.5-0.6	1391
0.6-0.7	449
0.7-0.8	47
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8633	High Similarity	NPD7236	Approved
0.8333	Intermediate Similarity	NPD7239	Suspended
0.8195	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6273	Approved
0.8148	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD7008	Discontinued
0.7947	Intermediate Similarity	NPD7058	Phase 2
0.7947	Intermediate Similarity	NPD7057	Phase 3
0.7891	Intermediate Similarity	NPD5951	Approved
0.7879	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6858	Approved
0.7874	Intermediate Similarity	NPD7094	Approved
0.7857	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7799	Discontinued
0.7786	Intermediate Similarity	NPD7741	Discontinued
0.777	Intermediate Similarity	NPD6663	Approved
0.7737	Intermediate Similarity	NPD5736	Approved
0.7669	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2629	Approved
0.7603	Intermediate Similarity	NPD4628	Phase 3
0.7589	Intermediate Similarity	NPD4140	Approved
0.7571	Intermediate Similarity	NPD3764	Approved
0.7537	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD7961	Discontinued
0.7483	Intermediate Similarity	NPD7003	Approved
0.7444	Intermediate Similarity	NPD7610	Discontinued
0.7424	Intermediate Similarity	NPD4198	Discontinued
0.7422	Intermediate Similarity	NPD2182	Approved
0.7422	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8127	Discontinued
0.7388	Intermediate Similarity	NPD7009	Phase 2
0.7355	Intermediate Similarity	NPD5761	Phase 2
0.7355	Intermediate Similarity	NPD5760	Phase 2
0.7339	Intermediate Similarity	NPD1238	Approved
0.732	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1930	Approved
0.7302	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1929	Approved
0.7299	Intermediate Similarity	NPD6287	Discontinued
0.7297	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6085	Phase 2
0.7285	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6004	Phase 3
0.7279	Intermediate Similarity	NPD6005	Phase 3
0.7279	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6002	Phase 3
0.7279	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6685	Approved
0.7259	Intermediate Similarity	NPD9545	Approved
0.7212	Intermediate Similarity	NPD6764	Approved
0.7212	Intermediate Similarity	NPD6765	Approved
0.72	Intermediate Similarity	NPD2066	Phase 3
0.7162	Intermediate Similarity	NPD5763	Approved
0.7162	Intermediate Similarity	NPD5762	Approved
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD8032	Phase 2
0.7143	Intermediate Similarity	NPD1876	Approved
0.7133	Intermediate Similarity	NPD8166	Discontinued
0.7132	Intermediate Similarity	NPD3091	Approved
0.7109	Intermediate Similarity	NPD164	Approved
0.7109	Intermediate Similarity	NPD5909	Discontinued
0.7109	Intermediate Similarity	NPD1237	Approved
0.7097	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5735	Approved
0.705	Intermediate Similarity	NPD3092	Approved
0.7047	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6785	Approved
0.7041	Intermediate Similarity	NPD6784	Approved
0.7031	Intermediate Similarity	NPD6647	Phase 2
0.7031	Intermediate Similarity	NPD5765	Approved
0.703	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2932	Approved
0.7029	Intermediate Similarity	NPD5126	Approved
0.7029	Intermediate Similarity	NPD5125	Phase 3
0.7029	Intermediate Similarity	NPD3095	Discontinued
0.7027	Intermediate Similarity	NPD7305	Phase 1
0.7027	Intermediate Similarity	NPD2799	Discontinued
0.7015	Intermediate Similarity	NPD6010	Discontinued
0.7007	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7638	Approved
0.695	Remote Similarity	NPD5327	Phase 3
0.6944	Remote Similarity	NPD7055	Discontinued
0.6939	Remote Similarity	NPD6355	Discontinued
0.6933	Remote Similarity	NPD2346	Discontinued
0.6929	Remote Similarity	NPD7640	Approved
0.6929	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD2798	Approved
0.6923	Remote Similarity	NPD4624	Approved
0.6918	Remote Similarity	NPD7713	Phase 3
0.6918	Remote Similarity	NPD7819	Suspended
0.6908	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3750	Approved
0.6905	Remote Similarity	NPD8368	Discontinued
0.6901	Remote Similarity	NPD1283	Approved
0.6899	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6353	Approved
0.6882	Remote Similarity	NPD8407	Phase 2
0.688	Remote Similarity	NPD1693	Approved
0.6879	Remote Similarity	NPD3226	Approved
0.6879	Remote Similarity	NPD1608	Approved
0.6879	Remote Similarity	NPD3972	Approved
0.6867	Remote Similarity	NPD5404	Approved
0.6867	Remote Similarity	NPD5406	Approved
0.6867	Remote Similarity	NPD5408	Approved
0.6867	Remote Similarity	NPD5405	Approved
0.6866	Remote Similarity	NPD6912	Phase 3
0.6857	Remote Similarity	NPD3023	Approved
0.6857	Remote Similarity	NPD3026	Approved
0.6855	Remote Similarity	NPD1088	Approved
0.6853	Remote Similarity	NPD2797	Approved
0.6853	Remote Similarity	NPD3094	Phase 2
0.6849	Remote Similarity	NPD2313	Discontinued
0.6848	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4766	Approved
0.6835	Remote Similarity	NPD7028	Phase 2
0.6835	Remote Similarity	NPD3024	Approved
0.6835	Remote Similarity	NPD3025	Approved
0.6835	Remote Similarity	NPD6599	Discontinued
0.6832	Remote Similarity	NPD7768	Phase 2
0.6826	Remote Similarity	NPD5844	Phase 1
0.6825	Remote Similarity	NPD1989	Approved
0.6822	Remote Similarity	NPD1932	Approved
0.6813	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1201	Approved
0.6803	Remote Similarity	NPD7714	Approved
0.6803	Remote Similarity	NPD7715	Approved
0.6802	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8434	Phase 2
0.68	Remote Similarity	NPD3748	Approved
0.68	Remote Similarity	NPD7033	Discontinued
0.6797	Remote Similarity	NPD4110	Phase 3
0.6797	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5048	Discontinued
0.6792	Remote Similarity	NPD7411	Suspended
0.6767	Remote Similarity	NPD2329	Discontinued
0.6757	Remote Similarity	NPD3620	Phase 2
0.6757	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2935	Discontinued
0.6755	Remote Similarity	NPD2796	Approved
0.6753	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.675	Remote Similarity	NPD37	Approved
0.674	Remote Similarity	NPD7497	Discontinued
0.6739	Remote Similarity	NPD9493	Approved
0.6739	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1470	Approved
0.6735	Remote Similarity	NPD6798	Discontinued
0.6731	Remote Similarity	NPD2532	Approved
0.6731	Remote Similarity	NPD2534	Approved
0.6731	Remote Similarity	NPD2533	Approved
0.6728	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD4965	Approved
0.6728	Remote Similarity	NPD4967	Phase 2
0.6724	Remote Similarity	NPD8361	Approved
0.6724	Remote Similarity	NPD8435	Approved
0.6724	Remote Similarity	NPD8360	Approved
0.6719	Remote Similarity	NPD9495	Approved
0.6716	Remote Similarity	NPD2067	Discontinued
0.6706	Remote Similarity	NPD7685	Pre-registration
0.6694	Remote Similarity	NPD1086	Approved
0.6694	Remote Similarity	NPD1090	Approved
0.6694	Remote Similarity	NPD9256	Approved
0.6694	Remote Similarity	NPD1089	Approved
0.6694	Remote Similarity	NPD9258	Approved
0.669	Remote Similarity	NPD1281	Approved
0.669	Remote Similarity	NPD5647	Approved
0.6689	Remote Similarity	NPD4308	Phase 3
0.6687	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1202	Approved
0.6667	Remote Similarity	NPD5306	Approved
0.6667	Remote Similarity	NPD2199	Approved
0.6667	Remote Similarity	NPD4059	Approved
0.6667	Remote Similarity	NPD2198	Approved
0.6667	Remote Similarity	NPD7199	Phase 2
0.6647	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6801	Discontinued
0.6645	Remote Similarity	NPD4477	Approved
0.6645	Remote Similarity	NPD4476	Approved
0.6645	Remote Similarity	NPD1551	Phase 2
0.6645	Remote Similarity	NPD7137	Phase 2
0.6644	Remote Similarity	NPD2979	Phase 3
0.6643	Remote Similarity	NPD4878	Approved
0.6641	Remote Similarity	NPD3495	Discontinued
0.6625	Remote Similarity	NPD4380	Phase 2
0.6622	Remote Similarity	NPD3268	Approved
0.6622	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6362	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