NPASS Compound

Structure

NPC472656 OpenBabel07101719252D 38 43 0 0 1 0 0 0 0 0999 V2000 8.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9527 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5348 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -1.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 1.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1847 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1847 1.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4527 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 2.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7807 1.8259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 -2.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4527 1.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9886 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -0.6522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5867 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4527 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 0.8478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 2.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 -1.1522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8546 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3187 -2.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 3.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 1.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 30 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 21 2 0 0 0 0 17 28 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 19 37 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 22 31 1 6 0 0 0 23 31 1 0 0 0 0 23 33 1 0 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 25 32 1 1 0 0 0 26 30 1 0 0 0 0 26 34 2 0 0 0 0 27 33 1 6 0 0 0 27 38 1 0 0 0 0 28 35 2 0 0 0 0 28 37 1 0 0 0 0 29 36 2 0 0 0 0 29 38 1 0 0 0 0 31 3 1 6 0 0 0 32 4 1 1 0 0 0 33 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.29
Volume:	550.845
LogP:	5.557
LogD:	4.598
LogS:	-5.267
# Rotatable Bonds:	4
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	4.794
Fsp3:	0.576
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.205
MDCK Permeability:	2.5443938284297474e-05
Pgp-inhibitor:	0.912
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	100.52108001708984%
Volume Distribution (VD):	1.279
Pgp-substrate:	3.0599069595336914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.261
CYP2C19-inhibitor:	0.631
CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.338
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.188
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.644
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	10.23
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.248
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.627
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.071
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.473
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC472656

Natural Product ID:	NPC472656
*Common Name:**	JVJYIUSSJCBVHK-SZDGHHOWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JVJYIUSSJCBVHK-SZDGHHOWSA-N
Standard InCHI:	InChI=1S/C33H40O5/c1-30(2)25-18-27(38-29(36)20-9-7-6-8-10-20)33(5)23-12-11-22(21-17-28(35)37-19-21)31(23,3)15-13-24(33)32(25,4)16-14-26(30)34/h6-10,12,17,22,24-25,27H,11,13-16,18-19H2,1-5H3/t22-,24+,25-,27+,31-,32+,33-/m0/s1
SMILES:	CC1(C2CC(C3(C(C2(CCC1=O)C)CCC4(C3=CCC4C5=CC(=O)OC5)C)C)OC(=O)C6=CC=CC=C6)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581393
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO32927.1	Dysoxylum mollissimum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25781655]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI	<	50.0	%	PMID[474756]
NPT168	Cell Line	P388	Mus musculus	GI	<	50.0	%	PMID[474756]
NPT116	Cell Line	HL-60	Homo sapiens	GI	<	50.0	%	PMID[474756]

☑ 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 NPC472656 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	310
0.1-0.2	1350
0.2-0.3	2188
0.3-0.4	5342
0.4-0.5	10782
0.5-0.6	14432
0.6-0.7	6998
0.7-0.8	1125
0.8-0.85	154
0.85-0.9	12
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.916	High Similarity	NPC126516
0.916	High Similarity	NPC329913
0.9098	High Similarity	NPC475373
0.9077	High Similarity	NPC470278
0.9015	High Similarity	NPC203486
0.8915	High Similarity	NPC473220
0.8915	High Similarity	NPC470753
0.8837	High Similarity	NPC470765
0.8731	High Similarity	NPC48929
0.8714	High Similarity	NPC475552
0.8696	High Similarity	NPC475135
0.8592	High Similarity	NPC473403
0.8571	High Similarity	NPC147561
0.855	High Similarity	NPC275576
0.8516	High Similarity	NPC473243
0.8485	Intermediate Similarity	NPC169913
0.8478	Intermediate Similarity	NPC210591
0.8478	Intermediate Similarity	NPC475652
0.8478	Intermediate Similarity	NPC214550
0.8451	Intermediate Similarity	NPC473602
0.845	Intermediate Similarity	NPC50872
0.8417	Intermediate Similarity	NPC43241
0.8417	Intermediate Similarity	NPC473613
0.8417	Intermediate Similarity	NPC473758
0.8417	Intermediate Similarity	NPC473109
0.8417	Intermediate Similarity	NPC473060
0.8417	Intermediate Similarity	NPC473085
0.8417	Intermediate Similarity	NPC48017
0.8417	Intermediate Similarity	NPC147880
0.8417	Intermediate Similarity	NPC184747
0.8417	Intermediate Similarity	NPC473081
0.8417	Intermediate Similarity	NPC4341
0.8417	Intermediate Similarity	NPC211137
0.8417	Intermediate Similarity	NPC200592
0.8417	Intermediate Similarity	NPC476094
0.8417	Intermediate Similarity	NPC473112
0.8406	Intermediate Similarity	NPC183122
0.8406	Intermediate Similarity	NPC283375
0.837	Intermediate Similarity	NPC72915
0.8357	Intermediate Similarity	NPC224491
0.8345	Intermediate Similarity	NPC472371
0.8345	Intermediate Similarity	NPC279442
0.8345	Intermediate Similarity	NPC472395
0.8321	Intermediate Similarity	NPC474608
0.832	Intermediate Similarity	NPC128368
0.8311	Intermediate Similarity	NPC25351
0.831	Intermediate Similarity	NPC470231
0.8309	Intermediate Similarity	NPC472394
0.8286	Intermediate Similarity	NPC475400
0.8276	Intermediate Similarity	NPC254558
0.8271	Intermediate Similarity	NPC476599
0.8261	Intermediate Similarity	NPC472577
0.8261	Intermediate Similarity	NPC473399
0.8261	Intermediate Similarity	NPC291638
0.8261	Intermediate Similarity	NPC195647
0.8261	Intermediate Similarity	NPC477893
0.8261	Intermediate Similarity	NPC473216
0.8261	Intermediate Similarity	NPC17877
0.8261	Intermediate Similarity	NPC477896
0.8261	Intermediate Similarity	NPC66761
0.8261	Intermediate Similarity	NPC471864
0.8252	Intermediate Similarity	NPC472556
0.8239	Intermediate Similarity	NPC139067
0.8239	Intermediate Similarity	NPC147217
0.8239	Intermediate Similarity	NPC91703
0.8239	Intermediate Similarity	NPC191082
0.8239	Intermediate Similarity	NPC270498
0.8239	Intermediate Similarity	NPC473673
0.8239	Intermediate Similarity	NPC246480
0.8239	Intermediate Similarity	NPC475429
0.8239	Intermediate Similarity	NPC177340
0.8201	Intermediate Similarity	NPC472545
0.8201	Intermediate Similarity	NPC472551
0.8188	Intermediate Similarity	NPC4242
0.8188	Intermediate Similarity	NPC471911
0.8182	Intermediate Similarity	NPC475122
0.8182	Intermediate Similarity	NPC11685
0.8182	Intermediate Similarity	NPC163719
0.8182	Intermediate Similarity	NPC188865
0.8182	Intermediate Similarity	NPC25768
0.8182	Intermediate Similarity	NPC472569
0.8182	Intermediate Similarity	NPC57628
0.8182	Intermediate Similarity	NPC70716
0.8182	Intermediate Similarity	NPC125106
0.8182	Intermediate Similarity	NPC67777
0.8182	Intermediate Similarity	NPC472570
0.8182	Intermediate Similarity	NPC51314
0.8182	Intermediate Similarity	NPC476974
0.8182	Intermediate Similarity	NPC472573
0.8182	Intermediate Similarity	NPC95265
0.8182	Intermediate Similarity	NPC95810
0.8175	Intermediate Similarity	NPC238370
0.8162	Intermediate Similarity	NPC475138
0.8156	Intermediate Similarity	NPC234548
0.8156	Intermediate Similarity	NPC248287
0.8156	Intermediate Similarity	NPC79921
0.8151	Intermediate Similarity	NPC7095
0.8151	Intermediate Similarity	NPC112216
0.8143	Intermediate Similarity	NPC39549
0.8125	Intermediate Similarity	NPC471104
0.8125	Intermediate Similarity	NPC200471
0.8125	Intermediate Similarity	NPC174982
0.8125	Intermediate Similarity	NPC472572
0.8125	Intermediate Similarity	NPC476973
0.8125	Intermediate Similarity	NPC96903
0.8125	Intermediate Similarity	NPC472571
0.8125	Intermediate Similarity	NPC471107
0.8125	Intermediate Similarity	NPC158663
0.8125	Intermediate Similarity	NPC171525
0.8125	Intermediate Similarity	NPC29704
0.8125	Intermediate Similarity	NPC184817
0.8125	Intermediate Similarity	NPC473088
0.8125	Intermediate Similarity	NPC469349
0.8125	Intermediate Similarity	NPC472575
0.8125	Intermediate Similarity	NPC472568
0.8125	Intermediate Similarity	NPC470159
0.8125	Intermediate Similarity	NPC70403
0.8125	Intermediate Similarity	NPC470157
0.8125	Intermediate Similarity	NPC177940
0.8125	Intermediate Similarity	NPC471100
0.8112	Intermediate Similarity	NPC95449
0.8112	Intermediate Similarity	NPC131966
0.8112	Intermediate Similarity	NPC191387
0.8112	Intermediate Similarity	NPC163087
0.8112	Intermediate Similarity	NPC477468
0.8108	Intermediate Similarity	NPC472657
0.8108	Intermediate Similarity	NPC472658
0.8099	Intermediate Similarity	NPC266374
0.8099	Intermediate Similarity	NPC16912
0.8082	Intermediate Similarity	NPC60509
0.8082	Intermediate Similarity	NPC473215
0.8082	Intermediate Similarity	NPC81698
0.8082	Intermediate Similarity	NPC250046
0.8074	Intermediate Similarity	NPC473423
0.8071	Intermediate Similarity	NPC472374
0.8071	Intermediate Similarity	NPC472372
0.8056	Intermediate Similarity	NPC470152
0.8056	Intermediate Similarity	NPC241951
0.8056	Intermediate Similarity	NPC475759
0.8054	Intermediate Similarity	NPC473611
0.8054	Intermediate Similarity	NPC282239
0.8042	Intermediate Similarity	NPC472546
0.8042	Intermediate Similarity	NPC183540
0.8042	Intermediate Similarity	NPC182869
0.8041	Intermediate Similarity	NPC477905
0.8039	Intermediate Similarity	NPC471003
0.8028	Intermediate Similarity	NPC171207
0.8028	Intermediate Similarity	NPC100913
0.8028	Intermediate Similarity	NPC97667
0.8028	Intermediate Similarity	NPC477904
0.8028	Intermediate Similarity	NPC472547
0.8028	Intermediate Similarity	NPC275592
0.8028	Intermediate Similarity	NPC90614
0.8028	Intermediate Similarity	NPC183270
0.8027	Intermediate Similarity	NPC473214
0.8027	Intermediate Similarity	NPC31829
0.8027	Intermediate Similarity	NPC477483
0.8027	Intermediate Similarity	NPC161239
0.8027	Intermediate Similarity	NPC470245
0.8027	Intermediate Similarity	NPC325032
0.8027	Intermediate Similarity	NPC198455
0.8027	Intermediate Similarity	NPC165260
0.8027	Intermediate Similarity	NPC125033
0.8015	Intermediate Similarity	NPC115797
0.8015	Intermediate Similarity	NPC51448
0.8014	Intermediate Similarity	NPC281717
0.8014	Intermediate Similarity	NPC262324
0.8	Intermediate Similarity	NPC106895
0.8	Intermediate Similarity	NPC469636
0.8	Intermediate Similarity	NPC127857
0.8	Intermediate Similarity	NPC217091
0.8	Intermediate Similarity	NPC152812
0.7987	Intermediate Similarity	NPC472022
0.7987	Intermediate Similarity	NPC472005
0.7987	Intermediate Similarity	NPC265395
0.7987	Intermediate Similarity	NPC237549
0.7987	Intermediate Similarity	NPC158333
0.7987	Intermediate Similarity	NPC249471
0.7987	Intermediate Similarity	NPC473414
0.7987	Intermediate Similarity	NPC256142
0.7987	Intermediate Similarity	NPC257213
0.7987	Intermediate Similarity	NPC304876
0.7987	Intermediate Similarity	NPC77719
0.7987	Intermediate Similarity	NPC1173
0.7987	Intermediate Similarity	NPC472030
0.7987	Intermediate Similarity	NPC242262
0.7986	Intermediate Similarity	NPC477894
0.7973	Intermediate Similarity	NPC51602
0.7972	Intermediate Similarity	NPC472576
0.7972	Intermediate Similarity	NPC41481
0.7972	Intermediate Similarity	NPC27377
0.7972	Intermediate Similarity	NPC56197
0.7972	Intermediate Similarity	NPC118080
0.7972	Intermediate Similarity	NPC291599
0.7972	Intermediate Similarity	NPC97947
0.7972	Intermediate Similarity	NPC87448
0.7959	Intermediate Similarity	NPC270590
0.7959	Intermediate Similarity	NPC476975
0.7959	Intermediate Similarity	NPC92293
0.7959	Intermediate Similarity	NPC301556

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 NPC472656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	866
0.2-0.3	1224
0.3-0.4	2775
0.4-0.5	2381
0.5-0.6	1337
0.6-0.7	273
0.7-0.8	23
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8511	High Similarity	NPD7236	Approved
0.8219	Intermediate Similarity	NPD7239	Suspended
0.7955	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD7961	Discontinued
0.777	Intermediate Similarity	NPD7008	Discontinued
0.777	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD7094	Approved
0.7752	Intermediate Similarity	NPD6858	Approved
0.7734	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7058	Phase 2
0.7727	Intermediate Similarity	NPD7057	Phase 3
0.7625	Intermediate Similarity	NPD7799	Discontinued
0.76	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7463	Intermediate Similarity	NPD7610	Discontinued
0.7451	Intermediate Similarity	NPD7458	Discontinued
0.7445	Intermediate Similarity	NPD6287	Discontinued
0.7442	Intermediate Similarity	NPD2182	Approved
0.7415	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD8032	Phase 2
0.7368	Intermediate Similarity	NPD5951	Approved
0.7292	Intermediate Similarity	NPD6663	Approved
0.7292	Intermediate Similarity	NPD7713	Phase 3
0.7273	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7003	Approved
0.7222	Intermediate Similarity	NPD1238	Approved
0.7205	Intermediate Similarity	NPD8127	Discontinued
0.7176	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3972	Approved
0.7133	Intermediate Similarity	NPD5736	Approved
0.7132	Intermediate Similarity	NPD164	Approved
0.7111	Intermediate Similarity	NPD2629	Approved
0.7083	Intermediate Similarity	NPD7055	Discontinued
0.7063	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4198	Discontinued
0.7042	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD4628	Phase 3
0.7029	Intermediate Similarity	NPD7741	Discontinued
0.6978	Remote Similarity	NPD3025	Approved
0.6978	Remote Similarity	NPD3024	Approved
0.6974	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7819	Suspended
0.6933	Remote Similarity	NPD7305	Phase 1
0.6923	Remote Similarity	NPD1930	Approved
0.6923	Remote Similarity	NPD6647	Phase 2
0.6923	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1929	Approved
0.6899	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3026	Approved
0.6879	Remote Similarity	NPD3023	Approved
0.6871	Remote Similarity	NPD3764	Approved
0.6867	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2067	Discontinued
0.6861	Remote Similarity	NPD690	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2346	Discontinued
0.6832	Remote Similarity	NPD5760	Phase 2
0.6832	Remote Similarity	NPD5761	Phase 2
0.6824	Remote Similarity	NPD8368	Discontinued
0.6824	Remote Similarity	NPD6765	Approved
0.6824	Remote Similarity	NPD6764	Approved
0.6822	Remote Similarity	NPD2066	Phase 3
0.6821	Remote Similarity	NPD2799	Discontinued
0.6821	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3019	Approved
0.6802	Remote Similarity	NPD8407	Phase 2
0.6786	Remote Similarity	NPD7009	Phase 2
0.6779	Remote Similarity	NPD2979	Phase 3
0.6779	Remote Similarity	NPD4140	Approved
0.6746	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8435	Approved
0.6743	Remote Similarity	NPD8360	Approved
0.6743	Remote Similarity	NPD8361	Approved
0.6742	Remote Similarity	NPD5909	Discontinued
0.6739	Remote Similarity	NPD4766	Approved
0.6736	Remote Similarity	NPD5327	Phase 3
0.6735	Remote Similarity	NPD6832	Phase 2
0.6732	Remote Similarity	NPD1471	Phase 3
0.6732	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8434	Phase 2
0.6719	Remote Similarity	NPD1989	Approved
0.6713	Remote Similarity	NPD1281	Approved
0.6712	Remote Similarity	NPD2798	Approved
0.6712	Remote Similarity	NPD6085	Phase 2
0.6712	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3748	Approved
0.6711	Remote Similarity	NPD7714	Approved
0.6711	Remote Similarity	NPD7715	Approved
0.6693	Remote Similarity	NPD1202	Approved
0.6692	Remote Similarity	NPD7798	Approved
0.6691	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2932	Approved
0.6689	Remote Similarity	NPD6039	Approved
0.6687	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD3495	Discontinued
0.6667	Remote Similarity	NPD5406	Approved
0.6667	Remote Similarity	NPD9545	Approved
0.6646	Remote Similarity	NPD6599	Discontinued
0.6646	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD7028	Phase 2
0.6644	Remote Similarity	NPD3267	Approved
0.6644	Remote Similarity	NPD2313	Discontinued
0.6644	Remote Similarity	NPD3266	Approved
0.6626	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6355	Discontinued
0.662	Remote Similarity	NPD5691	Approved
0.6617	Remote Similarity	NPD1237	Approved
0.6611	Remote Similarity	NPD8485	Approved
0.6605	Remote Similarity	NPD7411	Suspended
0.6597	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3226	Approved
0.6582	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7497	Discontinued
0.6575	Remote Similarity	NPD2199	Approved
0.6575	Remote Similarity	NPD2198	Approved
0.6575	Remote Similarity	NPD1283	Approved
0.6573	Remote Similarity	NPD17	Approved
0.6571	Remote Similarity	NPD3317	Approved
0.6568	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3887	Approved
0.6558	Remote Similarity	NPD2531	Phase 2
0.6558	Remote Similarity	NPD2935	Discontinued
0.6556	Remote Similarity	NPD4307	Phase 2
0.6552	Remote Similarity	NPD6637	Approved
0.6552	Remote Similarity	NPD4878	Approved
0.655	Remote Similarity	NPD5844	Phase 1
0.6538	Remote Similarity	NPD7179	Phase 2
0.6536	Remote Similarity	NPD2569	Approved
0.6536	Remote Similarity	NPD2567	Approved
0.6534	Remote Similarity	NPD8150	Discontinued
0.6533	Remote Similarity	NPD3268	Approved
0.6527	Remote Similarity	NPD5494	Approved
0.6525	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7075	Discontinued
0.6503	Remote Similarity	NPD5585	Approved
0.6503	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1651	Approved
0.6497	Remote Similarity	NPD4110	Phase 3
0.6497	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3750	Approved
0.6491	Remote Similarity	NPD7177	Discontinued
0.6491	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7631	Approved
0.648	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6353	Approved
0.6466	Remote Similarity	NPD1932	Approved
0.6463	Remote Similarity	NPD5667	Approved
0.6461	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8312	Approved
0.6457	Remote Similarity	NPD8313	Approved
0.6447	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7084	Phase 3
0.6438	Remote Similarity	NPD2534	Approved
0.6438	Remote Similarity	NPD1608	Approved
0.6438	Remote Similarity	NPD2533	Approved
0.6438	Remote Similarity	NPD2532	Approved
0.6434	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7473	Discontinued
0.6429	Remote Similarity	NPD1241	Discontinued
0.6429	Remote Similarity	NPD7097	Phase 1
0.6424	Remote Similarity	NPD6798	Discontinued
0.6423	Remote Similarity	NPD2329	Discontinued
0.6419	Remote Similarity	NPD2797	Approved
0.6419	Remote Similarity	NPD1470	Approved
0.641	Remote Similarity	NPD5763	Approved
0.641	Remote Similarity	NPD5762	Approved
0.6406	Remote Similarity	NPD7609	Phase 3
0.6405	Remote Similarity	NPD5735	Approved
0.6405	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6677	Suspended
0.6402	Remote Similarity	NPD6873	Phase 2
0.64	Remote Similarity	NPD9259	Approved
0.64	Remote Similarity	NPD9257	Approved
0.6391	Remote Similarity	NPD6959	Discontinued
0.6387	Remote Similarity	NPD4308	Phase 3
0.6386	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD1693	Approved
0.6375	Remote Similarity	NPD6799	Approved
0.637	Remote Similarity	NPD1201	Approved
0.6369	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2347	Approved
0.6364	Remote Similarity	NPD6801	Discontinued

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