NPASS Compound

Structure

NPC12006 OpenBabel07101719512D 37 39 0 0 1 0 0 0 0 0999 V2000 -9.5622 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4282 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8301 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6962 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6962 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2321 -1.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4282 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5622 2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3660 -0.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2942 2.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5622 3.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3660 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9641 -1.8660 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 1 3 2 0 0 0 0 1 14 1 0 0 0 0 2 4 2 0 0 0 0 2 14 1 0 0 0 0 3 16 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 25 1 0 0 0 0 7 8 2 0 0 0 0 8 35 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 26 1 0 0 0 0 12 36 1 0 0 0 0 13 25 1 0 0 0 0 13 27 2 0 0 0 0 15 12 1 6 0 0 0 16 17 2 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 11 1 6 0 0 0 18 21 1 0 0 0 0 18 37 1 0 0 0 0 19 25 1 6 0 0 0 19 30 1 0 0 0 0 20 31 2 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 6 0 0 0 23 24 1 0 0 0 0 23 34 1 1 0 0 0 24 35 1 6 0 0 0 24 37 1 0 0 0 0 25 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.19
Volume:	502.314
LogP:	-0.185
LogD:	-0.318
LogS:	-1.735
# Rotatable Bonds:	10
TPSA:	203.44
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.071
Synthetic Accessibility Score:	5.032
Fsp3:	0.52
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.38
MDCK Permeability:	1.9990699001937173e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.908
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	54.046756744384766%
Volume Distribution (VD):	0.414
Pgp-substrate:	53.463619232177734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.599
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	3.944
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.951
Carcinogencity:	0.57
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC12006

Natural Product ID:	NPC12006
*Common Name:**	Canangafruiticoside E
IUPAC Name:	[(1S,3S,4S)-4-formyl-3-hydroxy-4-[(Z)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	XRPQSBLZOWCYLI-ZUTDVGCPSA-N
Standard InCHI:	InChI=1S/C25H32O12/c26-11-18-21(32)22(33)23(34)24(37-18)35-8-7-25(13-27)6-5-15(10-19(25)30)12-36-20(31)4-2-14-1-3-16(28)17(29)9-14/h1-4,7-9,13,15,18-19,21-24,26,28-30,32-34H,5-6,10-12H2/b4-2+,8-7-/t15-,18+,19-,21+,22-,23+,24+,25+/m0/s1
SMILES:	c1cc(c(cc1/C=C/C(=O)OC[C@H]1CC[C@@](/C=CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)(C=O)[C@H](C1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3262194
PubChem CID:	90676280
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
Others	7

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	-3.8	%	PMID[471273]
NPT2	Others	Unspecified	Inhibition	=	-8.5	%	PMID[471273]
NPT2	Others	Unspecified	Inhibition	=	9.3	%	PMID[471273]
NPT2	Others	Unspecified	Inhibition	=	11.4	%	PMID[471273]
NPT2	Others	Unspecified	Inhibition	=	12.2	%	PMID[471273]
NPT2	Others	Unspecified	Inhibition	>	100.0	%	PMID[471273]
NPT27	Others	Unspecified	Activity	>	95.2	%	PMID[471273]

☑ 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 NPC12006 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	349
0.1-0.2	1304
0.2-0.3	2937
0.3-0.4	6036
0.4-0.5	9919
0.5-0.6	8106
0.6-0.7	9601
0.7-0.8	4124
0.8-0.85	293
0.85-0.9	25
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC471869
0.9281	High Similarity	NPC471873
0.8987	High Similarity	NPC471870
0.8926	High Similarity	NPC28776
0.8926	High Similarity	NPC473138
0.882	High Similarity	NPC471871
0.8776	High Similarity	NPC296643
0.8758	High Similarity	NPC471874
0.8699	High Similarity	NPC220942
0.8693	High Similarity	NPC106818
0.869	High Similarity	NPC470572
0.8681	High Similarity	NPC287597
0.8681	High Similarity	NPC34293
0.8681	High Similarity	NPC886
0.8645	High Similarity	NPC131532
0.8636	High Similarity	NPC87403
0.863	High Similarity	NPC260425
0.8621	High Similarity	NPC123988
0.8621	High Similarity	NPC158325
0.8621	High Similarity	NPC180171
0.8621	High Similarity	NPC103398
0.8621	High Similarity	NPC476870
0.8618	High Similarity	NPC478242
0.8592	High Similarity	NPC229784
0.8592	High Similarity	NPC477294
0.8592	High Similarity	NPC477293
0.8571	High Similarity	NPC472350
0.8571	High Similarity	NPC68092
0.8571	High Similarity	NPC197316
0.8571	High Similarity	NPC321638
0.8571	High Similarity	NPC321184
0.8571	High Similarity	NPC476383
0.8571	High Similarity	NPC81515
0.8571	High Similarity	NPC205195
0.8571	High Similarity	NPC64141
0.8571	High Similarity	NPC171134
0.8571	High Similarity	NPC89105
0.8571	High Similarity	NPC328273
0.8562	High Similarity	NPC471872
0.8562	High Similarity	NPC154485
0.8543	High Similarity	NPC320734
0.8542	High Similarity	NPC473285
0.8526	High Similarity	NPC475484
0.8521	High Similarity	NPC232880
0.8503	High Similarity	NPC310252
0.8503	High Similarity	NPC78363
0.8503	High Similarity	NPC476376
0.8503	High Similarity	NPC84789
0.8503	High Similarity	NPC302583
0.8503	High Similarity	NPC100558
0.8481	Intermediate Similarity	NPC469384
0.8481	Intermediate Similarity	NPC469654
0.8472	Intermediate Similarity	NPC219677
0.8467	Intermediate Similarity	NPC204644
0.8462	Intermediate Similarity	NPC472127
0.8462	Intermediate Similarity	NPC472128
0.8456	Intermediate Similarity	NPC476385
0.8456	Intermediate Similarity	NPC134405
0.8456	Intermediate Similarity	NPC47471
0.8456	Intermediate Similarity	NPC476377
0.8456	Intermediate Similarity	NPC186406
0.8451	Intermediate Similarity	NPC476873
0.8446	Intermediate Similarity	NPC62800
0.8446	Intermediate Similarity	NPC324262
0.8442	Intermediate Similarity	NPC69367
0.8431	Intermediate Similarity	NPC23677
0.8428	Intermediate Similarity	NPC44507
0.8425	Intermediate Similarity	NPC471883
0.8425	Intermediate Similarity	NPC106406
0.8421	Intermediate Similarity	NPC473867
0.8418	Intermediate Similarity	NPC187205
0.8418	Intermediate Similarity	NPC223335
0.8418	Intermediate Similarity	NPC475663
0.8418	Intermediate Similarity	NPC286919
0.8418	Intermediate Similarity	NPC40920
0.8415	Intermediate Similarity	NPC469774
0.8415	Intermediate Similarity	NPC32723
0.8415	Intermediate Similarity	NPC469775
0.8415	Intermediate Similarity	NPC469773
0.8415	Intermediate Similarity	NPC469777
0.8415	Intermediate Similarity	NPC469778
0.8415	Intermediate Similarity	NPC135334
0.8415	Intermediate Similarity	NPC469776
0.8415	Intermediate Similarity	NPC469772
0.8415	Intermediate Similarity	NPC100925
0.8415	Intermediate Similarity	NPC295941
0.8414	Intermediate Similarity	NPC473924
0.8411	Intermediate Similarity	NPC232228
0.8411	Intermediate Similarity	NPC296659
0.8411	Intermediate Similarity	NPC202391
0.8411	Intermediate Similarity	NPC292443
0.8408	Intermediate Similarity	NPC172920
0.8408	Intermediate Similarity	NPC156624
0.8405	Intermediate Similarity	NPC476017
0.84	Intermediate Similarity	NPC140502
0.84	Intermediate Similarity	NPC222433
0.84	Intermediate Similarity	NPC265648
0.8397	Intermediate Similarity	NPC299706
0.8397	Intermediate Similarity	NPC115466
0.8397	Intermediate Similarity	NPC245615
0.8397	Intermediate Similarity	NPC61604
0.8389	Intermediate Similarity	NPC475530
0.8389	Intermediate Similarity	NPC473799
0.8387	Intermediate Similarity	NPC140151
0.8377	Intermediate Similarity	NPC92117
0.8377	Intermediate Similarity	NPC111785
0.8375	Intermediate Similarity	NPC477627
0.8366	Intermediate Similarity	NPC470330
0.8365	Intermediate Similarity	NPC179914
0.8356	Intermediate Similarity	NPC254398
0.8355	Intermediate Similarity	NPC476382
0.8355	Intermediate Similarity	NPC34927
0.8355	Intermediate Similarity	NPC100998
0.8355	Intermediate Similarity	NPC475528
0.8355	Intermediate Similarity	NPC252292
0.8355	Intermediate Similarity	NPC34587
0.8354	Intermediate Similarity	NPC475058
0.8354	Intermediate Similarity	NPC478055
0.8345	Intermediate Similarity	NPC476407
0.8344	Intermediate Similarity	NPC247032
0.8344	Intermediate Similarity	NPC76406
0.8344	Intermediate Similarity	NPC476384
0.8344	Intermediate Similarity	NPC112
0.8344	Intermediate Similarity	NPC191046
0.8344	Intermediate Similarity	NPC96795
0.8344	Intermediate Similarity	NPC175214
0.8344	Intermediate Similarity	NPC476375
0.8344	Intermediate Similarity	NPC40305
0.8344	Intermediate Similarity	NPC476397
0.8344	Intermediate Similarity	NPC478239
0.8344	Intermediate Similarity	NPC298257
0.8344	Intermediate Similarity	NPC476381
0.8344	Intermediate Similarity	NPC264632
0.8344	Intermediate Similarity	NPC476378
0.8344	Intermediate Similarity	NPC194095
0.8344	Intermediate Similarity	NPC476380
0.8344	Intermediate Similarity	NPC205864
0.8344	Intermediate Similarity	NPC327032
0.8344	Intermediate Similarity	NPC119537
0.8344	Intermediate Similarity	NPC105005
0.8344	Intermediate Similarity	NPC269141
0.8333	Intermediate Similarity	NPC203664
0.8323	Intermediate Similarity	NPC469418
0.8323	Intermediate Similarity	NPC145847
0.8312	Intermediate Similarity	NPC120621
0.8312	Intermediate Similarity	NPC248257
0.8312	Intermediate Similarity	NPC116229
0.8311	Intermediate Similarity	NPC471345
0.8311	Intermediate Similarity	NPC157554
0.8311	Intermediate Similarity	NPC472132
0.831	Intermediate Similarity	NPC126991
0.831	Intermediate Similarity	NPC83218
0.8302	Intermediate Similarity	NPC226759
0.8302	Intermediate Similarity	NPC104275
0.8302	Intermediate Similarity	NPC4747
0.8302	Intermediate Similarity	NPC471878
0.8301	Intermediate Similarity	NPC212808
0.8301	Intermediate Similarity	NPC474268
0.8301	Intermediate Similarity	NPC199928
0.8301	Intermediate Similarity	NPC143246
0.8301	Intermediate Similarity	NPC119773
0.8301	Intermediate Similarity	NPC475539
0.8299	Intermediate Similarity	NPC169398
0.8291	Intermediate Similarity	NPC38699
0.8289	Intermediate Similarity	NPC476867
0.8289	Intermediate Similarity	NPC63304
0.8289	Intermediate Similarity	NPC196063
0.8289	Intermediate Similarity	NPC64195
0.8289	Intermediate Similarity	NPC183824
0.8289	Intermediate Similarity	NPC300894
0.8289	Intermediate Similarity	NPC141455
0.8289	Intermediate Similarity	NPC296954
0.8289	Intermediate Similarity	NPC110063
0.8282	Intermediate Similarity	NPC469419
0.828	Intermediate Similarity	NPC157898
0.828	Intermediate Similarity	NPC215811
0.8278	Intermediate Similarity	NPC157816
0.8276	Intermediate Similarity	NPC470122
0.8276	Intermediate Similarity	NPC17968
0.8276	Intermediate Similarity	NPC469705
0.8272	Intermediate Similarity	NPC100420
0.8272	Intermediate Similarity	NPC109990
0.8267	Intermediate Similarity	NPC179505
0.8267	Intermediate Similarity	NPC156709
0.8267	Intermediate Similarity	NPC471875
0.8267	Intermediate Similarity	NPC202700
0.8263	Intermediate Similarity	NPC469397
0.8252	Intermediate Similarity	NPC471157
0.8247	Intermediate Similarity	NPC232992
0.8239	Intermediate Similarity	NPC471405
0.8239	Intermediate Similarity	NPC163635
0.8239	Intermediate Similarity	NPC228357
0.8235	Intermediate Similarity	NPC476864
0.8235	Intermediate Similarity	NPC287615
0.8235	Intermediate Similarity	NPC83743
0.8235	Intermediate Similarity	NPC216819
0.8235	Intermediate Similarity	NPC476866
0.8235	Intermediate Similarity	NPC476869
0.8235	Intermediate Similarity	NPC262182
0.8235	Intermediate Similarity	NPC476868

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 NPC12006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	815
0.2-0.3	1769
0.3-0.4	2726
0.4-0.5	2038
0.5-0.6	1078
0.6-0.7	386
0.7-0.8	47
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7266	Discontinued
0.8105	Intermediate Similarity	NPD6190	Approved
0.7917	Intermediate Similarity	NPD7074	Phase 3
0.7911	Intermediate Similarity	NPD1653	Approved
0.7904	Intermediate Similarity	NPD3818	Discontinued
0.7904	Intermediate Similarity	NPD7228	Approved
0.7857	Intermediate Similarity	NPD7054	Approved
0.7824	Intermediate Similarity	NPD7685	Pre-registration
0.7824	Intermediate Similarity	NPD6559	Discontinued
0.7811	Intermediate Similarity	NPD7472	Approved
0.7806	Intermediate Similarity	NPD8166	Discontinued
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.7778	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7251	Discontinued
0.7716	Intermediate Similarity	NPD37	Approved
0.7683	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4965	Approved
0.7683	Intermediate Similarity	NPD4966	Approved
0.7661	Intermediate Similarity	NPD6797	Phase 2
0.7644	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD8312	Approved
0.763	Intermediate Similarity	NPD8313	Approved
0.7572	Intermediate Similarity	NPD7808	Phase 3
0.7547	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD1934	Approved
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7240	Approved
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.7368	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6166	Phase 2
0.7368	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.7257	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7473	Discontinued
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7202	Intermediate Similarity	NPD3817	Phase 2
0.7195	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6674	Discontinued
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD2801	Approved
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1511	Approved
0.711	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1551	Phase 2
0.7107	Intermediate Similarity	NPD2935	Discontinued
0.7101	Intermediate Similarity	NPD5402	Approved
0.7097	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1933	Approved
0.7067	Intermediate Similarity	NPD1091	Approved
0.7059	Intermediate Similarity	NPD3882	Suspended
0.7051	Intermediate Similarity	NPD6663	Approved
0.7041	Intermediate Similarity	NPD7819	Suspended
0.7041	Intermediate Similarity	NPD1465	Phase 2
0.7037	Intermediate Similarity	NPD7680	Approved
0.703	Intermediate Similarity	NPD1512	Approved
0.7017	Intermediate Similarity	NPD8150	Discontinued
0.7013	Intermediate Similarity	NPD9494	Approved
0.7013	Intermediate Similarity	NPD5736	Approved
0.7006	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD943	Approved
0.6989	Remote Similarity	NPD3751	Discontinued
0.6988	Remote Similarity	NPD5403	Approved
0.6982	Remote Similarity	NPD6801	Discontinued
0.6981	Remote Similarity	NPD7097	Phase 1
0.6968	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6599	Discontinued
0.6964	Remote Similarity	NPD7028	Phase 2
0.6962	Remote Similarity	NPD6355	Discontinued
0.6962	Remote Similarity	NPD447	Suspended
0.6949	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7435	Discontinued
0.6933	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1549	Phase 2
0.6913	Remote Similarity	NPD9545	Approved
0.6911	Remote Similarity	NPD8320	Phase 1
0.6911	Remote Similarity	NPD8319	Approved
0.6908	Remote Similarity	NPD9269	Phase 2
0.6906	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3455	Phase 2
0.6903	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD9570	Approved
0.6893	Remote Similarity	NPD7799	Discontinued
0.6879	Remote Similarity	NPD3764	Approved
0.6879	Remote Similarity	NPD6798	Discontinued
0.6867	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD1357	Approved
0.6857	Remote Similarity	NPD3787	Discontinued
0.6856	Remote Similarity	NPD8151	Discontinued
0.6852	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5494	Approved
0.6835	Remote Similarity	NPD6233	Phase 2
0.6832	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1510	Phase 2
0.6832	Remote Similarity	NPD7033	Discontinued
0.6826	Remote Similarity	NPD6273	Approved
0.6824	Remote Similarity	NPD7411	Suspended
0.6815	Remote Similarity	NPD7095	Approved
0.681	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6799	Approved
0.6806	Remote Similarity	NPD6823	Phase 2
0.6805	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3620	Phase 2
0.6792	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6534	Approved
0.6791	Remote Similarity	NPD6535	Approved
0.679	Remote Similarity	NPD6099	Approved
0.679	Remote Similarity	NPD5406	Approved
0.679	Remote Similarity	NPD5405	Approved
0.679	Remote Similarity	NPD5408	Approved
0.679	Remote Similarity	NPD6100	Approved
0.679	Remote Similarity	NPD5404	Approved
0.6789	Remote Similarity	NPD6780	Approved
0.6789	Remote Similarity	NPD6778	Approved
0.6789	Remote Similarity	NPD6777	Approved
0.6789	Remote Similarity	NPD6781	Approved
0.6789	Remote Similarity	NPD6782	Approved
0.6789	Remote Similarity	NPD6779	Approved
0.6789	Remote Similarity	NPD6776	Approved
0.6772	Remote Similarity	NPD7699	Phase 2
0.6772	Remote Similarity	NPD7700	Phase 2
0.6772	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7768	Phase 2
0.6757	Remote Similarity	NPD2629	Approved
0.674	Remote Similarity	NPD8368	Discontinued
0.6735	Remote Similarity	NPD7874	Approved
0.6735	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3750	Approved
0.6711	Remote Similarity	NPD1778	Approved
0.6709	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6653	Approved
0.6706	Remote Similarity	NPD3226	Approved
0.6705	Remote Similarity	NPD5353	Approved
0.6701	Remote Similarity	NPD7783	Phase 2
0.6701	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2861	Phase 2
0.6687	Remote Similarity	NPD4060	Phase 1
0.6687	Remote Similarity	NPD2438	Suspended
0.6687	Remote Similarity	NPD826	Approved
0.6687	Remote Similarity	NPD825	Approved
0.6684	Remote Similarity	NPD7696	Phase 3
0.6684	Remote Similarity	NPD7697	Approved
0.6684	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD9493	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6213	Phase 3
0.6649	Remote Similarity	NPD7870	Phase 2
0.6649	Remote Similarity	NPD6212	Phase 3
0.6649	Remote Similarity	NPD7871	Phase 2
0.6649	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7038	Approved
0.6648	Remote Similarity	NPD7039	Approved
0.6647	Remote Similarity	NPD5761	Phase 2
0.6647	Remote Similarity	NPD5760	Phase 2
0.6646	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD6832	Phase 2
0.6646	Remote Similarity	NPD5763	Approved
0.6646	Remote Similarity	NPD2346	Discontinued
0.6645	Remote Similarity	NPD9268	Approved
0.6644	Remote Similarity	NPD3022	Approved
0.6644	Remote Similarity	NPD3021	Approved
0.6633	Remote Similarity	NPD7701	Phase 2
0.663	Remote Similarity	NPD8407	Phase 2
0.6628	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6385	Approved
0.6628	Remote Similarity	NPD6386	Approved
0.6627	Remote Similarity	NPD7003	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