NPASS Compound

Structure

NPC220664 OpenBabel07101718242D 36 38 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2321 5.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2321 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 6.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 4.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 5.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 7.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 5.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 1 14 2 0 0 0 0 2 7 2 0 0 0 0 2 14 1 0 0 0 0 3 8 2 0 0 0 0 3 15 1 0 0 0 0 4 9 2 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 25 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 19 29 1 1 0 0 0 20 23 1 0 0 0 0 20 35 1 6 0 0 0 21 30 2 0 0 0 0 21 35 1 0 0 0 0 22 31 2 0 0 0 0 22 36 1 0 0 0 0 23 32 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 24 1 6 0 0 0 25 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.13
Volume:	482.978
LogP:	2.025
LogD:	0.403
LogS:	-2.092
# Rotatable Bonds:	9
TPSA:	191.05
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.183
Synthetic Accessibility Score:	4.065
Fsp3:	0.24
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.307
MDCK Permeability:	1.6174570191651583e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.957
Human Intestinal Absorption (HIA):	0.525
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	98.13030242919922%
Volume Distribution (VD):	0.326
Pgp-substrate:	1.3848028182983398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.151
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.618
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.478
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	2.859
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.206
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.357
Skin Sensitization:	0.922
Carcinogencity:	0.183
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC220664

Natural Product ID:	NPC220664
*Common Name:**	1-O-Trans-Caffeoyl-5-O-Trans-P-Coumaroylquinic Acid
IUPAC Name:	(1S,3R,4R,5R)-1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	SZQUAPJIXVTPBU-ZQQDKFTKSA-N
Standard InCHI:	InChI=1S/C25H24O11/c26-16-6-1-14(2-7-16)4-9-21(30)35-20-13-25(24(33)34,12-19(29)23(20)32)36-22(31)10-5-15-3-8-17(27)18(28)11-15/h1-11,19-20,23,26-29,32H,12-13H2,(H,33,34)/b9-4+,10-5+/t19-,20-,23-,25+/m1/s1
SMILES:	c1cc(ccc1/C=C/C(=O)O[C@@H]1C[C@@](C[C@H]([C@H]1O)O)(C(=O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2349421
PubChem CID:	71719612
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic 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
NPO33307	pimpinella brachycarpa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23462643]

☑ 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	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	94.3	%	PMID[452724]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	23530.0	nM	PMID[452724]

☑ 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 NPC220664 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	330
0.1-0.2	1314
0.2-0.3	3226
0.3-0.4	7444
0.4-0.5	10235
0.5-0.6	5757
0.6-0.7	8436
0.7-0.8	5560
0.8-0.85	270
0.85-0.9	56
0.9-0.95	27
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC284948
1.0	High Similarity	NPC319628
1.0	High Similarity	NPC303090
1.0	High Similarity	NPC37331
0.9926	High Similarity	NPC206095
0.9926	High Similarity	NPC477335
0.9926	High Similarity	NPC224389
0.9926	High Similarity	NPC297517
0.9926	High Similarity	NPC35702
0.9926	High Similarity	NPC471027
0.9926	High Similarity	NPC13818
0.9853	High Similarity	NPC277315
0.9853	High Similarity	NPC472016
0.9853	High Similarity	NPC43158
0.9853	High Similarity	NPC192831
0.9853	High Similarity	NPC258469
0.9704	High Similarity	NPC219428
0.9704	High Similarity	NPC152942
0.9704	High Similarity	NPC283560
0.9704	High Similarity	NPC302857
0.9704	High Similarity	NPC37250
0.9704	High Similarity	NPC24295
0.9704	High Similarity	NPC278068
0.9704	High Similarity	NPC142703
0.9643	High Similarity	NPC471076
0.9643	High Similarity	NPC192568
0.9632	High Similarity	NPC474875
0.9632	High Similarity	NPC476820
0.9632	High Similarity	NPC26241
0.9632	High Similarity	NPC274891
0.9632	High Similarity	NPC303683
0.9632	High Similarity	NPC476819
0.9632	High Similarity	NPC295492
0.9632	High Similarity	NPC205751
0.9568	High Similarity	NPC477333
0.9437	High Similarity	NPC42464
0.9433	High Similarity	NPC322660
0.9407	High Similarity	NPC68517
0.9371	High Similarity	NPC306343
0.9366	High Similarity	NPC43123
0.9338	High Similarity	NPC182217
0.9338	High Similarity	NPC233350
0.9338	High Similarity	NPC70680
0.9306	High Similarity	NPC477334
0.9241	High Similarity	NPC93498
0.9241	High Similarity	NPC163883
0.9225	High Similarity	NPC98356
0.9178	High Similarity	NPC19380
0.9178	High Similarity	NPC146277
0.9122	High Similarity	NPC470896
0.9122	High Similarity	NPC473275
0.9118	High Similarity	NPC61
0.9118	High Similarity	NPC25581
0.9118	High Similarity	NPC18074
0.9118	High Similarity	NPC5419
0.9085	High Similarity	NPC50221
0.9085	High Similarity	NPC114242
0.9071	High Similarity	NPC179505
0.9071	High Similarity	NPC156709
0.9054	High Similarity	NPC145425
0.9051	High Similarity	NPC168799
0.9051	High Similarity	NPC155209
0.9044	High Similarity	NPC198388
0.9041	High Similarity	NPC252979
0.9028	High Similarity	NPC229264
0.8951	High Similarity	NPC226738
0.8951	High Similarity	NPC22176
0.8951	High Similarity	NPC190587
0.8951	High Similarity	NPC121573
0.8929	High Similarity	NPC279676
0.8929	High Similarity	NPC67349
0.8873	High Similarity	NPC38473
0.8867	High Similarity	NPC134925
0.8849	High Similarity	NPC474895
0.8836	High Similarity	NPC142528
0.8811	High Similarity	NPC477277
0.8811	High Similarity	NPC477278
0.8792	High Similarity	NPC44730
0.8741	High Similarity	NPC477279
0.8714	High Similarity	NPC106406
0.8707	High Similarity	NPC120621
0.8707	High Similarity	NPC248257
0.8696	High Similarity	NPC217052
0.8696	High Similarity	NPC329344
0.8696	High Similarity	NPC237506
0.8696	High Similarity	NPC32626
0.869	High Similarity	NPC160378
0.8675	High Similarity	NPC203757
0.8671	High Similarity	NPC75763
0.8671	High Similarity	NPC225036
0.8671	High Similarity	NPC288452
0.8671	High Similarity	NPC12218
0.8671	High Similarity	NPC289690
0.8671	High Similarity	NPC105525
0.8658	High Similarity	NPC140151
0.8649	High Similarity	NPC75945
0.8649	High Similarity	NPC92117
0.8645	High Similarity	NPC227297
0.8643	High Similarity	NPC471749
0.8639	High Similarity	NPC283081
0.8639	High Similarity	NPC299090
0.8639	High Similarity	NPC221383
0.8639	High Similarity	NPC143892
0.8633	High Similarity	NPC318799
0.8601	High Similarity	NPC239943
0.86	High Similarity	NPC246566
0.86	High Similarity	NPC95498
0.8591	High Similarity	NPC259576
0.8591	High Similarity	NPC221091
0.8591	High Similarity	NPC32197
0.8581	High Similarity	NPC472969
0.8571	High Similarity	NPC473867
0.8562	High Similarity	NPC474692
0.8543	High Similarity	NPC16024
0.8543	High Similarity	NPC61152
0.8543	High Similarity	NPC205037
0.8543	High Similarity	NPC3746
0.8543	High Similarity	NPC44260
0.854	High Similarity	NPC475695
0.8535	High Similarity	NPC471823
0.8533	High Similarity	NPC300329
0.8531	High Similarity	NPC84789
0.8531	High Similarity	NPC302583
0.8531	High Similarity	NPC100558
0.8531	High Similarity	NPC310252
0.8523	High Similarity	NPC476394
0.8523	High Similarity	NPC98809
0.8503	High Similarity	NPC53884
0.8503	High Similarity	NPC258671
0.85	High Similarity	NPC108553
0.8489	Intermediate Similarity	NPC94810
0.8483	Intermediate Similarity	NPC9218
0.8481	Intermediate Similarity	NPC128403
0.8477	Intermediate Similarity	NPC75695
0.8477	Intermediate Similarity	NPC106818
0.8456	Intermediate Similarity	NPC98009
0.8451	Intermediate Similarity	NPC34293
0.8451	Intermediate Similarity	NPC886
0.8451	Intermediate Similarity	NPC248150
0.8451	Intermediate Similarity	NPC287597
0.8435	Intermediate Similarity	NPC304956
0.8435	Intermediate Similarity	NPC229036
0.8435	Intermediate Similarity	NPC470130
0.8421	Intermediate Similarity	NPC475216
0.8421	Intermediate Similarity	NPC87403
0.8421	Intermediate Similarity	NPC475595
0.8421	Intermediate Similarity	NPC475162
0.8421	Intermediate Similarity	NPC83663
0.8421	Intermediate Similarity	NPC266084
0.8421	Intermediate Similarity	NPC475145
0.8421	Intermediate Similarity	NPC473544
0.8411	Intermediate Similarity	NPC243891
0.8406	Intermediate Similarity	NPC168653
0.8406	Intermediate Similarity	NPC251407
0.8394	Intermediate Similarity	NPC85565
0.8392	Intermediate Similarity	NPC123988
0.8392	Intermediate Similarity	NPC18646
0.8387	Intermediate Similarity	NPC471750
0.8387	Intermediate Similarity	NPC74319
0.8387	Intermediate Similarity	NPC287872
0.8378	Intermediate Similarity	NPC108455
0.8377	Intermediate Similarity	NPC247629
0.8377	Intermediate Similarity	NPC239019
0.8366	Intermediate Similarity	NPC477299
0.8366	Intermediate Similarity	NPC125487
0.8366	Intermediate Similarity	NPC191046
0.8366	Intermediate Similarity	NPC194095
0.8366	Intermediate Similarity	NPC327032
0.8366	Intermediate Similarity	NPC281703
0.8357	Intermediate Similarity	NPC226855
0.8355	Intermediate Similarity	NPC476434
0.8355	Intermediate Similarity	NPC267091
0.8345	Intermediate Similarity	NPC328273
0.8345	Intermediate Similarity	NPC321184
0.8345	Intermediate Similarity	NPC321638
0.8345	Intermediate Similarity	NPC171134
0.8345	Intermediate Similarity	NPC284409
0.8344	Intermediate Similarity	NPC473091
0.8344	Intermediate Similarity	NPC4013
0.8344	Intermediate Similarity	NPC144557
0.8344	Intermediate Similarity	NPC90905
0.8333	Intermediate Similarity	NPC156892
0.8333	Intermediate Similarity	NPC289346
0.8333	Intermediate Similarity	NPC301089
0.8333	Intermediate Similarity	NPC24164
0.8333	Intermediate Similarity	NPC28776
0.8333	Intermediate Similarity	NPC473138
0.8333	Intermediate Similarity	NPC44507
0.8333	Intermediate Similarity	NPC132921
0.8323	Intermediate Similarity	NPC156818
0.8323	Intermediate Similarity	NPC226759
0.8323	Intermediate Similarity	NPC40920
0.8323	Intermediate Similarity	NPC472860
0.8323	Intermediate Similarity	NPC38779
0.8323	Intermediate Similarity	NPC133984
0.8323	Intermediate Similarity	NPC68324
0.8323	Intermediate Similarity	NPC223335
0.8323	Intermediate Similarity	NPC160512
0.8323	Intermediate Similarity	NPC114179
0.8323	Intermediate Similarity	NPC289322

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 NPC220664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	785
0.2-0.3	1698
0.3-0.4	2766
0.4-0.5	2020
0.5-0.6	1058
0.6-0.7	457
0.7-0.8	80
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6190	Approved
0.8258	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD230	Phase 1
0.8219	Intermediate Similarity	NPD7266	Discontinued
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3817	Phase 2
0.7799	Intermediate Similarity	NPD3882	Suspended
0.7791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6166	Phase 2
0.7791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6233	Phase 2
0.7736	Intermediate Similarity	NPD5402	Approved
0.773	Intermediate Similarity	NPD9269	Phase 2
0.7725	Intermediate Similarity	NPD7685	Pre-registration
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7673	Intermediate Similarity	NPD2801	Approved
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7662	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7075	Discontinued
0.7619	Intermediate Similarity	NPD7251	Discontinued
0.761	Intermediate Similarity	NPD1934	Approved
0.7593	Intermediate Similarity	NPD6234	Discontinued
0.759	Intermediate Similarity	NPD3751	Discontinued
0.7582	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD8166	Discontinued
0.758	Intermediate Similarity	NPD1653	Approved
0.7564	Intermediate Similarity	NPD1512	Approved
0.7562	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3764	Approved
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD3027	Phase 3
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.7469	Intermediate Similarity	NPD4965	Approved
0.7469	Intermediate Similarity	NPD4967	Phase 2
0.7469	Intermediate Similarity	NPD4966	Approved
0.7455	Intermediate Similarity	NPD6232	Discontinued
0.7455	Intermediate Similarity	NPD3787	Discontinued
0.7453	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.745	Intermediate Similarity	NPD943	Approved
0.7447	Intermediate Similarity	NPD9268	Approved
0.744	Intermediate Similarity	NPD7054	Approved
0.7436	Intermediate Similarity	NPD1511	Approved
0.7436	Intermediate Similarity	NPD6799	Approved
0.7432	Intermediate Similarity	NPD6798	Discontinued
0.7431	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5403	Approved
0.7399	Intermediate Similarity	NPD8150	Discontinued
0.7396	Intermediate Similarity	NPD7472	Approved
0.7396	Intermediate Similarity	NPD7074	Phase 3
0.7381	Intermediate Similarity	NPD7228	Approved
0.7347	Intermediate Similarity	NPD9494	Approved
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.7321	Intermediate Similarity	NPD7473	Discontinued
0.7317	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3455	Phase 2
0.7289	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD5401	Approved
0.7255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7095	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD6599	Discontinued
0.7152	Intermediate Similarity	NPD4062	Phase 3
0.7135	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6385	Approved
0.7117	Intermediate Similarity	NPD6386	Approved
0.7105	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2935	Discontinued
0.7083	Intermediate Similarity	NPD8127	Discontinued
0.7067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4340	Discontinued
0.7032	Intermediate Similarity	NPD1510	Phase 2
0.7032	Intermediate Similarity	NPD7033	Discontinued
0.703	Intermediate Similarity	NPD7819	Suspended
0.7027	Intermediate Similarity	NPD7435	Discontinued
0.7024	Intermediate Similarity	NPD5494	Approved
0.7012	Intermediate Similarity	NPD7411	Suspended
0.7006	Intermediate Similarity	NPD1549	Phase 2
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4060	Phase 1
0.6988	Remote Similarity	NPD5353	Approved
0.6987	Remote Similarity	NPD9570	Approved
0.6961	Remote Similarity	NPD6535	Approved
0.6961	Remote Similarity	NPD6534	Approved
0.6957	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD447	Suspended
0.6944	Remote Similarity	NPD5536	Phase 2
0.6943	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8455	Phase 2
0.6918	Remote Similarity	NPD3750	Approved
0.6914	Remote Similarity	NPD7038	Approved
0.6914	Remote Similarity	NPD6559	Discontinued
0.6914	Remote Similarity	NPD7039	Approved
0.6914	Remote Similarity	NPD7240	Approved
0.6901	Remote Similarity	NPD5242	Approved
0.6899	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8320	Phase 1
0.6898	Remote Similarity	NPD8319	Approved
0.6892	Remote Similarity	NPD1608	Approved
0.6883	Remote Similarity	NPD825	Approved
0.6883	Remote Similarity	NPD826	Approved
0.6879	Remote Similarity	NPD1551	Phase 2
0.6875	Remote Similarity	NPD3887	Approved
0.6875	Remote Similarity	NPD2354	Approved
0.6865	Remote Similarity	NPD6782	Approved
0.6865	Remote Similarity	NPD6780	Approved
0.6865	Remote Similarity	NPD6778	Approved
0.6865	Remote Similarity	NPD6777	Approved
0.6865	Remote Similarity	NPD6781	Approved
0.6865	Remote Similarity	NPD6779	Approved
0.6865	Remote Similarity	NPD6776	Approved
0.6864	Remote Similarity	NPD919	Approved
0.6857	Remote Similarity	NPD3021	Approved
0.6857	Remote Similarity	NPD3022	Approved
0.6853	Remote Similarity	NPD2629	Approved
0.6852	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3146	Approved
0.6852	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7699	Phase 2
0.6848	Remote Similarity	NPD7700	Phase 2
0.6836	Remote Similarity	NPD8312	Approved
0.6836	Remote Similarity	NPD8313	Approved
0.6824	Remote Similarity	NPD1535	Discovery
0.6818	Remote Similarity	NPD6663	Approved
0.6813	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4110	Phase 3
0.6813	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7874	Approved
0.6806	Remote Similarity	NPD4198	Discontinued
0.6806	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3749	Approved
0.68	Remote Similarity	NPD3225	Approved
0.6792	Remote Similarity	NPD4534	Discontinued
0.6792	Remote Similarity	NPD5958	Discontinued
0.679	Remote Similarity	NPD4357	Discontinued
0.6788	Remote Similarity	NPD3226	Approved
0.6786	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1247	Approved
0.6779	Remote Similarity	NPD1481	Phase 2
0.6776	Remote Similarity	NPD5736	Approved
0.6774	Remote Similarity	NPD1240	Approved
0.6772	Remote Similarity	NPD5408	Approved
0.6772	Remote Similarity	NPD5406	Approved
0.6772	Remote Similarity	NPD2796	Approved
0.6772	Remote Similarity	NPD5404	Approved
0.6772	Remote Similarity	NPD5405	Approved
0.6763	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7097	Phase 1
0.6748	Remote Similarity	NPD2532	Approved
0.6748	Remote Similarity	NPD2534	Approved
0.6748	Remote Similarity	NPD2533	Approved
0.6746	Remote Similarity	NPD7768	Phase 2
0.6738	Remote Similarity	NPD2067	Discontinued
0.6731	Remote Similarity	NPD555	Phase 2
0.673	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7236	Approved
0.6723	Remote Similarity	NPD8368	Discontinued
0.6709	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6273	Approved
0.6705	Remote Similarity	NPD3926	Phase 2
0.6704	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD17	Approved
0.6688	Remote Similarity	NPD6653	Approved
0.6688	Remote Similarity	NPD1607	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7458	Discontinued
0.6686	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3450	Approved
0.6649	Remote Similarity	NPD3452	Approved
0.6649	Remote Similarity	NPD2493	Approved
0.6649	Remote Similarity	NPD2494	Approved
0.6648	Remote Similarity	NPD8361	Approved
0.6648	Remote Similarity	NPD8435	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