NPASS Compound

Structure

NPC471872 OpenBabel07101718292D 29 31 0 0 1 0 0 0 0 0999 V2000 0.8731 -1.8252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6759 2.9144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8891 -2.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0501 -1.1272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7280 -3.0647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0501 -0.1585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2111 0.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3722 -0.1585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7280 -1.1272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3722 1.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4320 -0.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0501 1.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8891 -1.6116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2111 1.2946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5670 -2.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5670 -1.6116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5332 1.2946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8891 0.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4844 -0.8390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6482 0.7199 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5332 0.3259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4060 -3.0647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4060 -1.1272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6943 1.7790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7280 -0.1585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0903 -1.7240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2454 2.6151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8891 1.2946 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 14 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 17 1 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 28 1 0 0 0 0 14 12 1 6 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 6 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 26 1 6 0 0 0 19 29 1 0 0 0 0 20 21 1 1 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 21 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.18
Volume:	403.242
LogP:	2.191
LogD:	2.486
LogS:	-2.445
# Rotatable Bonds:	7
TPSA:	114.68
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	4.836
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.91
MDCK Permeability:	1.6213472918025218e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	81.0301742553711%
Volume Distribution (VD):	0.394
Pgp-substrate:	16.385446548461914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.196
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	11.867
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.847
Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.961
Carcinogencity:	0.781
Eye Corrosion:	0.004
Eye Irritation:	0.1
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC471872

Natural Product ID:	NPC471872
*Common Name:**	Canangaterpene I
IUPAC Name:	[(1S,3S,5S,6S,8S)-6-hydroxy-1,3-dimethoxy-2-oxaspiro[4.5]decan-8-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	FMROSSLNINUGJU-VOLPZXEBSA-N
Standard InCHI:	InChI=1S/C21H28O8/c1-26-19-11-21(20(27-2)29-19)8-7-14(10-17(21)24)12-28-18(25)6-4-13-3-5-15(22)16(23)9-13/h3-6,9,14,17,19-20,22-24H,7-8,10-12H2,1-2H3/b6-4+/t14-,17-,19-,20-,21-/m0/s1
SMILES:	CO[C@H]1O[C@@H](C[C@@]21CC[C@@H](C[C@@H]2O)COC(=O)/C=C/c1ccc(c(c1)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3262195
PubChem CID:	90676281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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	=	34.7	%	PMID[493239]
NPT2	Others	Unspecified	Inhibition	=	42.8	%	PMID[493239]
NPT2	Others	Unspecified	Inhibition	=	65.2	%	PMID[493239]
NPT2	Others	Unspecified	Inhibition	=	62.8	%	PMID[493239]
NPT2	Others	Unspecified	Inhibition	=	66.8	%	PMID[493239]
NPT2	Others	Unspecified	Inhibition	=	3.6	%	PMID[493239]
NPT27	Others	Unspecified	Activity	>	95.2	%	PMID[493239]

☑ 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 NPC471872 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	264
0.1-0.2	1120
0.2-0.3	2720
0.3-0.4	5875
0.4-0.5	11485
0.5-0.6	8736
0.6-0.7	9846
0.7-0.8	2395
0.8-0.85	227
0.85-0.9	27
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC154485
0.8889	High Similarity	NPC254398
0.8881	High Similarity	NPC219677
0.8841	High Similarity	NPC321184
0.8841	High Similarity	NPC171134
0.8841	High Similarity	NPC328273
0.8841	High Similarity	NPC321638
0.8824	High Similarity	NPC886
0.8824	High Similarity	NPC287597
0.8824	High Similarity	NPC34293
0.8824	High Similarity	NPC471883
0.8815	High Similarity	NPC473924
0.8803	High Similarity	NPC320734
0.8731	High Similarity	NPC229784
0.8731	High Similarity	NPC477293
0.8731	High Similarity	NPC477294
0.8705	High Similarity	NPC476383
0.8705	High Similarity	NPC472350
0.8705	High Similarity	NPC68092
0.8705	High Similarity	NPC89105
0.8705	High Similarity	NPC81515
0.8705	High Similarity	NPC197316
0.8705	High Similarity	NPC64141
0.8676	High Similarity	NPC473285
0.8662	High Similarity	NPC300894
0.8662	High Similarity	NPC296954
0.8662	High Similarity	NPC196063
0.8662	High Similarity	NPC141455
0.8657	High Similarity	NPC232880
0.8643	High Similarity	NPC471875
0.8633	High Similarity	NPC260425
0.8633	High Similarity	NPC78363
0.8615	High Similarity	NPC470848
0.8615	High Similarity	NPC470849
0.8592	High Similarity	NPC204644
0.8592	High Similarity	NPC105005
0.8592	High Similarity	NPC235557
0.8592	High Similarity	NPC40305
0.8582	High Similarity	NPC134405
0.8582	High Similarity	NPC476873
0.8582	High Similarity	NPC476385
0.8582	High Similarity	NPC476377
0.8582	High Similarity	NPC47471
0.8571	High Similarity	NPC226005
0.8571	High Similarity	NPC205195
0.8571	High Similarity	NPC220942
0.8562	High Similarity	NPC12006
0.8561	High Similarity	NPC470572
0.8561	High Similarity	NPC476699
0.8542	High Similarity	NPC229505
0.8531	High Similarity	NPC26045
0.8527	High Similarity	NPC309434
0.8521	High Similarity	NPC140502
0.8521	High Similarity	NPC265648
0.8521	High Similarity	NPC222433
0.8514	High Similarity	NPC471874
0.8511	High Similarity	NPC473591
0.8511	High Similarity	NPC473799
0.8511	High Similarity	NPC475530
0.8511	High Similarity	NPC271494
0.8511	High Similarity	NPC155192
0.85	High Similarity	NPC476376
0.8489	Intermediate Similarity	NPC476870
0.8462	Intermediate Similarity	NPC476384
0.8462	Intermediate Similarity	NPC109371
0.8462	Intermediate Similarity	NPC269141
0.8462	Intermediate Similarity	NPC76406
0.8462	Intermediate Similarity	NPC470214
0.8462	Intermediate Similarity	NPC263386
0.8462	Intermediate Similarity	NPC70084
0.8462	Intermediate Similarity	NPC310621
0.8462	Intermediate Similarity	NPC476375
0.8462	Intermediate Similarity	NPC96795
0.8462	Intermediate Similarity	NPC476381
0.8462	Intermediate Similarity	NPC112
0.8462	Intermediate Similarity	NPC476397
0.8462	Intermediate Similarity	NPC476378
0.8462	Intermediate Similarity	NPC205864
0.8462	Intermediate Similarity	NPC175214
0.8462	Intermediate Similarity	NPC476380
0.8462	Intermediate Similarity	NPC141791
0.8462	Intermediate Similarity	NPC298257
0.8462	Intermediate Similarity	NPC470215
0.8462	Intermediate Similarity	NPC119537
0.8462	Intermediate Similarity	NPC264632
0.8462	Intermediate Similarity	NPC247032
0.8456	Intermediate Similarity	NPC30174
0.8446	Intermediate Similarity	NPC478268
0.844	Intermediate Similarity	NPC182249
0.8429	Intermediate Similarity	NPC157554
0.8403	Intermediate Similarity	NPC64195
0.8403	Intermediate Similarity	NPC110063
0.8392	Intermediate Similarity	NPC35212
0.8392	Intermediate Similarity	NPC296643
0.8385	Intermediate Similarity	NPC86198
0.8385	Intermediate Similarity	NPC203124
0.8372	Intermediate Similarity	NPC281277
0.837	Intermediate Similarity	NPC471157
0.8357	Intermediate Similarity	NPC101624
0.8357	Intermediate Similarity	NPC184938
0.8345	Intermediate Similarity	NPC83743
0.8345	Intermediate Similarity	NPC34587
0.8345	Intermediate Similarity	NPC262182
0.8345	Intermediate Similarity	NPC216819
0.8345	Intermediate Similarity	NPC476382
0.8345	Intermediate Similarity	NPC34927
0.8345	Intermediate Similarity	NPC252292
0.8345	Intermediate Similarity	NPC100998
0.8345	Intermediate Similarity	NPC287615
0.8333	Intermediate Similarity	NPC478239
0.8333	Intermediate Similarity	NPC478255
0.8333	Intermediate Similarity	NPC252133
0.8322	Intermediate Similarity	NPC186406
0.8322	Intermediate Similarity	NPC473612
0.8311	Intermediate Similarity	NPC188393
0.8311	Intermediate Similarity	NPC470934
0.831	Intermediate Similarity	NPC100389
0.831	Intermediate Similarity	NPC116742
0.831	Intermediate Similarity	NPC139243
0.8309	Intermediate Similarity	NPC471881
0.8309	Intermediate Similarity	NPC288416
0.8309	Intermediate Similarity	NPC45224
0.8309	Intermediate Similarity	NPC471882
0.8309	Intermediate Similarity	NPC156692
0.8309	Intermediate Similarity	NPC173150
0.8309	Intermediate Similarity	NPC35288
0.8308	Intermediate Similarity	NPC200988
0.8308	Intermediate Similarity	NPC145023
0.8308	Intermediate Similarity	NPC175799
0.8308	Intermediate Similarity	NPC610
0.8296	Intermediate Similarity	NPC83218
0.8296	Intermediate Similarity	NPC126991
0.8296	Intermediate Similarity	NPC90318
0.8295	Intermediate Similarity	NPC233669
0.8295	Intermediate Similarity	NPC474967
0.8288	Intermediate Similarity	NPC199928
0.8286	Intermediate Similarity	NPC135127
0.8276	Intermediate Similarity	NPC292443
0.8276	Intermediate Similarity	NPC297342
0.8276	Intermediate Similarity	NPC232228
0.8271	Intermediate Similarity	NPC147654
0.8264	Intermediate Similarity	NPC157816
0.8264	Intermediate Similarity	NPC67467
0.8264	Intermediate Similarity	NPC52664
0.8261	Intermediate Similarity	NPC275950
0.8261	Intermediate Similarity	NPC173308
0.8261	Intermediate Similarity	NPC181079
0.8252	Intermediate Similarity	NPC470617
0.8252	Intermediate Similarity	NPC470616
0.8248	Intermediate Similarity	NPC225307
0.8244	Intermediate Similarity	NPC275519
0.8235	Intermediate Similarity	NPC94179
0.8235	Intermediate Similarity	NPC61181
0.8235	Intermediate Similarity	NPC478269
0.8231	Intermediate Similarity	NPC232992
0.8224	Intermediate Similarity	NPC228357
0.8224	Intermediate Similarity	NPC11411
0.8222	Intermediate Similarity	NPC474532
0.8222	Intermediate Similarity	NPC469568
0.8219	Intermediate Similarity	NPC163898
0.8217	Intermediate Similarity	NPC261453
0.8217	Intermediate Similarity	NPC33749
0.8217	Intermediate Similarity	NPC328593
0.8214	Intermediate Similarity	NPC169973
0.8209	Intermediate Similarity	NPC52097
0.8201	Intermediate Similarity	NPC46137
0.8201	Intermediate Similarity	NPC476345
0.8201	Intermediate Similarity	NPC235294
0.8194	Intermediate Similarity	NPC472711
0.8188	Intermediate Similarity	NPC470619
0.8188	Intermediate Similarity	NPC208785
0.8188	Intermediate Similarity	NPC145527
0.8188	Intermediate Similarity	NPC470618
0.8188	Intermediate Similarity	NPC267469
0.8188	Intermediate Similarity	NPC87630
0.8188	Intermediate Similarity	NPC477300
0.8188	Intermediate Similarity	NPC179128
0.8188	Intermediate Similarity	NPC116292
0.8182	Intermediate Similarity	NPC76032
0.8182	Intermediate Similarity	NPC132723
0.8176	Intermediate Similarity	NPC215095
0.8176	Intermediate Similarity	NPC261122
0.8176	Intermediate Similarity	NPC28776
0.8176	Intermediate Similarity	NPC300262
0.8176	Intermediate Similarity	NPC199311
0.8176	Intermediate Similarity	NPC80732
0.8176	Intermediate Similarity	NPC473138
0.8176	Intermediate Similarity	NPC201148
0.8176	Intermediate Similarity	NPC210611
0.8176	Intermediate Similarity	NPC192763
0.8176	Intermediate Similarity	NPC3460
0.8176	Intermediate Similarity	NPC28651
0.8175	Intermediate Similarity	NPC103533
0.8175	Intermediate Similarity	NPC264900
0.8175	Intermediate Similarity	NPC79715
0.8175	Intermediate Similarity	NPC231607
0.8175	Intermediate Similarity	NPC108659
0.8169	Intermediate Similarity	NPC186418
0.8169	Intermediate Similarity	NPC471988
0.8169	Intermediate Similarity	NPC120852

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 NPC471872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	729
0.2-0.3	1583
0.3-0.4	2743
0.4-0.5	2196
0.5-0.6	1243
0.6-0.7	409
0.7-0.8	32
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
0.8705	High Similarity	NPD7266	Discontinued
0.7891	Intermediate Similarity	NPD8166	Discontinued
0.7763	Intermediate Similarity	NPD1653	Approved
0.7658	Intermediate Similarity	NPD6234	Discontinued
0.7647	Intermediate Similarity	NPD1357	Approved
0.76	Intermediate Similarity	NPD6190	Approved
0.7564	Intermediate Similarity	NPD37	Approved
0.7557	Intermediate Similarity	NPD3022	Approved
0.7557	Intermediate Similarity	NPD3021	Approved
0.7546	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD4966	Approved
0.7532	Intermediate Similarity	NPD4965	Approved
0.7532	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD3818	Discontinued
0.7431	Intermediate Similarity	NPD3027	Phase 3
0.7413	Intermediate Similarity	NPD5736	Approved
0.7397	Intermediate Similarity	NPD3620	Phase 2
0.7397	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3094	Phase 2
0.7386	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4110	Phase 3
0.7294	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD4060	Phase 1
0.7262	Intermediate Similarity	NPD7685	Pre-registration
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7237	Intermediate Similarity	NPD6674	Discontinued
0.7234	Intermediate Similarity	NPD3092	Approved
0.723	Intermediate Similarity	NPD230	Phase 1
0.7211	Intermediate Similarity	NPD6663	Approved
0.7194	Intermediate Similarity	NPD3091	Approved
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7185	Intermediate Similarity	NPD969	Suspended
0.7163	Intermediate Similarity	NPD3496	Discontinued
0.7162	Intermediate Similarity	NPD1613	Approved
0.7162	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7134	Intermediate Similarity	NPD7199	Phase 2
0.7113	Intermediate Similarity	NPD3705	Approved
0.7107	Intermediate Similarity	NPD7028	Phase 2
0.7099	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4626	Approved
0.7083	Intermediate Similarity	NPD7054	Approved
0.7059	Intermediate Similarity	NPD7240	Approved
0.7059	Intermediate Similarity	NPD228	Approved
0.7044	Intermediate Similarity	NPD3455	Phase 2
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7041	Intermediate Similarity	NPD7472	Approved
0.7039	Intermediate Similarity	NPD2935	Discontinued
0.7025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5691	Approved
0.702	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7097	Phase 1
0.7018	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6797	Phase 2
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD5763	Approved
0.6993	Remote Similarity	NPD5762	Approved
0.6993	Remote Similarity	NPD1091	Approved
0.6978	Remote Similarity	NPD7157	Approved
0.6972	Remote Similarity	NPD3095	Discontinued
0.6962	Remote Similarity	NPD6273	Approved
0.6959	Remote Similarity	NPD7251	Discontinued
0.6959	Remote Similarity	NPD7095	Approved
0.6959	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5283	Phase 1
0.6954	Remote Similarity	NPD6653	Approved
0.6951	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3134	Approved
0.6933	Remote Similarity	NPD825	Approved
0.6933	Remote Similarity	NPD826	Approved
0.6906	Remote Similarity	NPD2629	Approved
0.6892	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1358	Approved
0.6887	Remote Similarity	NPD5735	Approved
0.6879	Remote Similarity	NPD5536	Phase 2
0.6871	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2977	Approved
0.6871	Remote Similarity	NPD2978	Approved
0.6871	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3020	Approved
0.6857	Remote Similarity	NPD4198	Discontinued
0.6853	Remote Similarity	NPD2932	Approved
0.6853	Remote Similarity	NPD5125	Phase 3
0.6853	Remote Similarity	NPD3019	Approved
0.6853	Remote Similarity	NPD5126	Approved
0.6824	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2861	Phase 2
0.6821	Remote Similarity	NPD7808	Phase 3
0.681	Remote Similarity	NPD1934	Approved
0.68	Remote Similarity	NPD3764	Approved
0.68	Remote Similarity	NPD6798	Discontinued
0.6792	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3882	Suspended
0.6783	Remote Similarity	NPD5585	Approved
0.6782	Remote Similarity	NPD8313	Approved
0.6782	Remote Similarity	NPD8312	Approved
0.678	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2859	Approved
0.6769	Remote Similarity	NPD2860	Approved
0.6768	Remote Similarity	NPD8455	Phase 2
0.6763	Remote Similarity	NPD7843	Approved
0.6758	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6233	Phase 2
0.6752	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1778	Approved
0.6731	Remote Similarity	NPD2424	Discontinued
0.6715	Remote Similarity	NPD2684	Approved
0.6713	Remote Similarity	NPD9545	Approved
0.6712	Remote Similarity	NPD9269	Phase 2
0.6711	Remote Similarity	NPD943	Approved
0.6711	Remote Similarity	NPD9494	Approved
0.671	Remote Similarity	NPD2438	Suspended
0.6706	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6166	Phase 2
0.6706	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7680	Approved
0.6692	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2934	Approved
0.6692	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2933	Approved
0.6689	Remote Similarity	NPD2797	Approved
0.6687	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD5327	Phase 3
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD555	Phase 2
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD5124	Phase 1
0.6648	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7003	Approved
0.6646	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4108	Discontinued
0.6644	Remote Similarity	NPD258	Approved
0.6644	Remote Similarity	NPD257	Approved
0.6644	Remote Similarity	NPD422	Phase 1
0.6643	Remote Similarity	NPD5535	Approved
0.6641	Remote Similarity	NPD844	Approved
0.6627	Remote Similarity	NPD3817	Phase 2
0.6626	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1283	Approved
0.6621	Remote Similarity	NPD9384	Approved
0.6621	Remote Similarity	NPD9381	Approved
0.6621	Remote Similarity	NPD4059	Approved
0.662	Remote Similarity	NPD6671	Approved
0.6611	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6032	Approved
0.6603	Remote Similarity	NPD9570	Approved
0.6601	Remote Similarity	NPD2979	Phase 3
0.6601	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3059	Approved
0.6601	Remote Similarity	NPD3062	Approved
0.6601	Remote Similarity	NPD3061	Approved
0.6591	Remote Similarity	NPD288	Approved
0.659	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6232	Discontinued
0.6585	Remote Similarity	NPD4380	Phase 2
0.6582	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1652	Phase 2
0.6579	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3268	Approved
0.6575	Remote Similarity	NPD3847	Discontinued
0.6573	Remote Similarity	NPD9493	Approved
0.6573	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8434	Phase 2
0.657	Remote Similarity	NPD7473	Discontinued
0.6566	Remote Similarity	NPD2801	Approved
0.6564	Remote Similarity	NPD3687	Approved
0.6564	Remote Similarity	NPD3686	Approved
0.6562	Remote Similarity	NPD7236	Approved
0.6561	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6005	Phase 3
0.6561	Remote Similarity	NPD6002	Phase 3
0.6561	Remote Similarity	NPD6004	Phase 3
0.6561	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD3657	Discovery
0.6558	Remote Similarity	NPD1933	Approved
0.6556	Remote Similarity	NPD4908	Phase 1
0.6554	Remote Similarity	NPD3685	Discontinued
0.6554	Remote Similarity	NPD4359	Approved
0.6554	Remote Similarity	NPD9622	Approved
0.6548	Remote Similarity	NPD7075	Discontinued
0.6547	Remote Similarity	NPD4750	Phase 3
0.6541	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7033	Discontinued
0.6538	Remote Similarity	NPD2799	Discontinued
0.6536	Remote Similarity	NPD4062	Phase 3
0.6536	Remote Similarity	NPD8032	Phase 2
0.6536	Remote Similarity	NPD259	Phase 1
0.6533	Remote Similarity	NPD6007	Clinical (unspecified phase)

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