NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	500.13
Volume:	482.978
LogP:	2.078
LogD:	1.141
LogS:	-2.316
# 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:	4.042
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:	-6.231
MDCK Permeability:	1.0298681445419788e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.486
Human Intestinal Absorption (HIA):	0.751
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	98.35277557373047%
Volume Distribution (VD):	0.228
Pgp-substrate:	1.065230131149292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.465
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.653
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	2.481
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.452
Drug-inuced Liver Injury (DILI):	0.488
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.943
Carcinogencity:	0.154
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC477335

Natural Product ID:	NPC477335
*Common Name:**	(1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
IUPAC Name:	(1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	PCMWSBGTYOCQCP-UMHPNHICSA-N
Standard InCHI:	InChI=1S/C25H24O11/c26-16-6-1-14(2-7-16)4-9-22(31)36-23-19(29)12-25(34,24(32)33)13-20(23)35-21(30)10-5-15-3-8-17(27)18(28)11-15/h1-11,19-20,23,26-29,34H,12-13H2,(H,32,33)/b9-4+,10-5+/t19-,20-,23+,25-/m1/s1
SMILES:	C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC=C(C=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	42598865
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
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730248]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	Leaves	Khon Kaen, Thailand	2002-APR	PMID[15921434]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	ground entire plants	Hainan Province, China	2004-APR	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21338052]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31017778]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	31700	nM	PMID[15921434]

☑ 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 NPC477335 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	327
0.1-0.2	1273
0.2-0.3	3194
0.3-0.4	7323
0.4-0.5	10285
0.5-0.6	5734
0.6-0.7	8324
0.7-0.8	5817
0.8-0.85	293
0.85-0.9	60
0.9-0.95	25
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471027
1.0	High Similarity	NPC297517
1.0	High Similarity	NPC224389
1.0	High Similarity	NPC35702
1.0	High Similarity	NPC13818
1.0	High Similarity	NPC206095
0.9926	High Similarity	NPC258469
0.9926	High Similarity	NPC284948
0.9926	High Similarity	NPC43158
0.9926	High Similarity	NPC277315
0.9926	High Similarity	NPC37331
0.9926	High Similarity	NPC220664
0.9926	High Similarity	NPC303090
0.9926	High Similarity	NPC319628
0.9926	High Similarity	NPC192831
0.9926	High Similarity	NPC472016
0.9776	High Similarity	NPC302857
0.9776	High Similarity	NPC37250
0.9776	High Similarity	NPC142703
0.9776	High Similarity	NPC278068
0.9776	High Similarity	NPC152942
0.9776	High Similarity	NPC219428
0.9704	High Similarity	NPC26241
0.9704	High Similarity	NPC295492
0.9704	High Similarity	NPC474875
0.9704	High Similarity	NPC476820
0.9704	High Similarity	NPC205751
0.9704	High Similarity	NPC274891
0.9704	High Similarity	NPC303683
0.9704	High Similarity	NPC476819
0.9638	High Similarity	NPC477333
0.963	High Similarity	NPC24295
0.963	High Similarity	NPC283560
0.9571	High Similarity	NPC192568
0.9571	High Similarity	NPC471076
0.9504	High Similarity	NPC42464
0.95	High Similarity	NPC322660
0.9478	High Similarity	NPC68517
0.9437	High Similarity	NPC306343
0.9433	High Similarity	NPC43123
0.9407	High Similarity	NPC233350
0.9407	High Similarity	NPC182217
0.9407	High Similarity	NPC70680
0.9306	High Similarity	NPC163883
0.9306	High Similarity	NPC93498
0.9291	High Similarity	NPC98356
0.9241	High Similarity	NPC19380
0.9241	High Similarity	NPC146277
0.9236	High Similarity	NPC477334
0.9149	High Similarity	NPC50221
0.9149	High Similarity	NPC114242
0.9116	High Similarity	NPC145425
0.9103	High Similarity	NPC252979
0.9054	High Similarity	NPC473275
0.9054	High Similarity	NPC470896
0.9044	High Similarity	NPC25581
0.9044	High Similarity	NPC18074
0.9044	High Similarity	NPC5419
0.9044	High Similarity	NPC61
0.9014	High Similarity	NPC22176
0.9014	High Similarity	NPC121573
0.9014	High Similarity	NPC226738
0.9014	High Similarity	NPC190587
0.9	High Similarity	NPC179505
0.9	High Similarity	NPC156709
0.8978	High Similarity	NPC168799
0.8978	High Similarity	NPC155209
0.8971	High Similarity	NPC198388
0.8958	High Similarity	NPC229264
0.8913	High Similarity	NPC474895
0.8897	High Similarity	NPC142528
0.8857	High Similarity	NPC67349
0.8857	High Similarity	NPC279676
0.8803	High Similarity	NPC38473
0.88	High Similarity	NPC134925
0.8777	High Similarity	NPC106406
0.8767	High Similarity	NPC120621
0.8767	High Similarity	NPC248257
0.8741	High Similarity	NPC477277
0.8741	High Similarity	NPC477278
0.8733	High Similarity	NPC203757
0.8732	High Similarity	NPC12218
0.8732	High Similarity	NPC75763
0.8732	High Similarity	NPC105525
0.8732	High Similarity	NPC225036
0.8725	High Similarity	NPC44730
0.8716	High Similarity	NPC140151
0.8707	High Similarity	NPC92117
0.8707	High Similarity	NPC75945
0.8705	High Similarity	NPC471749
0.8701	High Similarity	NPC227297
0.8696	High Similarity	NPC318799
0.8671	High Similarity	NPC477279
0.8662	High Similarity	NPC239943
0.8639	High Similarity	NPC472969
0.863	High Similarity	NPC473867
0.8623	High Similarity	NPC237506
0.8623	High Similarity	NPC32626
0.8623	High Similarity	NPC217052
0.8623	High Similarity	NPC329344
0.8621	High Similarity	NPC474692
0.8621	High Similarity	NPC160378
0.8603	High Similarity	NPC475695
0.8601	High Similarity	NPC289690
0.8601	High Similarity	NPC288452
0.86	High Similarity	NPC44260
0.86	High Similarity	NPC205037
0.86	High Similarity	NPC16024
0.86	High Similarity	NPC61152
0.86	High Similarity	NPC3746
0.8592	High Similarity	NPC302583
0.8592	High Similarity	NPC84789
0.8592	High Similarity	NPC310252
0.8592	High Similarity	NPC100558
0.859	High Similarity	NPC471823
0.8581	High Similarity	NPC98809
0.8581	High Similarity	NPC476394
0.8571	High Similarity	NPC283081
0.8571	High Similarity	NPC221383
0.8571	High Similarity	NPC143892
0.8571	High Similarity	NPC299090
0.8551	High Similarity	NPC94810
0.8542	High Similarity	NPC9218
0.8535	High Similarity	NPC128403
0.8533	High Similarity	NPC95498
0.8533	High Similarity	NPC106818
0.8533	High Similarity	NPC75695
0.8533	High Similarity	NPC246566
0.8523	High Similarity	NPC259576
0.8523	High Similarity	NPC221091
0.8523	High Similarity	NPC32197
0.8511	High Similarity	NPC886
0.8511	High Similarity	NPC287597
0.8511	High Similarity	NPC34293
0.8511	High Similarity	NPC248150
0.8493	Intermediate Similarity	NPC229036
0.8493	Intermediate Similarity	NPC470130
0.8477	Intermediate Similarity	NPC87403
0.8467	Intermediate Similarity	NPC243891
0.8467	Intermediate Similarity	NPC300329
0.8456	Intermediate Similarity	NPC85565
0.8451	Intermediate Similarity	NPC123988
0.8451	Intermediate Similarity	NPC18646
0.8442	Intermediate Similarity	NPC287872
0.8442	Intermediate Similarity	NPC74319
0.8435	Intermediate Similarity	NPC108455
0.8435	Intermediate Similarity	NPC258671
0.8435	Intermediate Similarity	NPC53884
0.8431	Intermediate Similarity	NPC239019
0.8431	Intermediate Similarity	NPC247629
0.8429	Intermediate Similarity	NPC108553
0.8421	Intermediate Similarity	NPC191046
0.8421	Intermediate Similarity	NPC327032
0.8421	Intermediate Similarity	NPC194095
0.8417	Intermediate Similarity	NPC226855
0.8411	Intermediate Similarity	NPC476434
0.8411	Intermediate Similarity	NPC267091
0.8403	Intermediate Similarity	NPC328273
0.8403	Intermediate Similarity	NPC321638
0.8403	Intermediate Similarity	NPC321184
0.8403	Intermediate Similarity	NPC171134
0.84	Intermediate Similarity	NPC473091
0.8397	Intermediate Similarity	NPC90905
0.8397	Intermediate Similarity	NPC4013
0.8392	Intermediate Similarity	NPC156892
0.8389	Intermediate Similarity	NPC98009
0.8389	Intermediate Similarity	NPC28776
0.8389	Intermediate Similarity	NPC473138
0.8387	Intermediate Similarity	NPC289346
0.8387	Intermediate Similarity	NPC24164
0.838	Intermediate Similarity	NPC135127
0.8378	Intermediate Similarity	NPC474465
0.8377	Intermediate Similarity	NPC114179
0.8377	Intermediate Similarity	NPC160512
0.8377	Intermediate Similarity	NPC172419
0.8377	Intermediate Similarity	NPC289322
0.8377	Intermediate Similarity	NPC156818
0.8377	Intermediate Similarity	NPC472860
0.8377	Intermediate Similarity	NPC226759
0.8377	Intermediate Similarity	NPC38779
0.8377	Intermediate Similarity	NPC238419
0.8377	Intermediate Similarity	NPC133984
0.8377	Intermediate Similarity	NPC68324
0.837	Intermediate Similarity	NPC472271
0.837	Intermediate Similarity	NPC147654
0.8367	Intermediate Similarity	NPC473090
0.8367	Intermediate Similarity	NPC183824
0.8367	Intermediate Similarity	NPC304956
0.8355	Intermediate Similarity	NPC266084
0.8355	Intermediate Similarity	NPC473544
0.8355	Intermediate Similarity	NPC475145
0.8355	Intermediate Similarity	NPC475216
0.8355	Intermediate Similarity	NPC83663
0.8355	Intermediate Similarity	NPC475595
0.8355	Intermediate Similarity	NPC475162
0.8333	Intermediate Similarity	NPC472859
0.8333	Intermediate Similarity	NPC25389
0.8333	Intermediate Similarity	NPC78363
0.8333	Intermediate Similarity	NPC478242
0.8333	Intermediate Similarity	NPC260425

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 NPC477335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	770
0.2-0.3	1688
0.3-0.4	2745
0.4-0.5	2034
0.5-0.6	1072
0.6-0.7	473
0.7-0.8	83
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
0.9926	High Similarity	NPD6190	Approved
0.8312	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD230	Phase 1
0.8276	Intermediate Similarity	NPD7266	Discontinued
0.8037	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6166	Phase 2
0.784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD9269	Phase 2
0.7785	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD7685	Pre-registration
0.7744	Intermediate Similarity	NPD3818	Discontinued
0.7736	Intermediate Similarity	NPD3882	Suspended
0.7722	Intermediate Similarity	NPD2801	Approved
0.7712	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD5402	Approved
0.7671	Intermediate Similarity	NPD6233	Phase 2
0.7658	Intermediate Similarity	NPD1934	Approved
0.764	Intermediate Similarity	NPD6234	Discontinued
0.7632	Intermediate Similarity	NPD8166	Discontinued
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7628	Intermediate Similarity	NPD1653	Approved
0.7613	Intermediate Similarity	NPD1512	Approved
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6797	Phase 2
0.7603	Intermediate Similarity	NPD3764	Approved
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7578	Intermediate Similarity	NPD7075	Discontinued
0.756	Intermediate Similarity	NPD7251	Discontinued
0.7554	Intermediate Similarity	NPD9545	Approved
0.7547	Intermediate Similarity	NPD37	Approved
0.7534	Intermediate Similarity	NPD3027	Phase 3
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.753	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4966	Approved
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD7054	Approved
0.7484	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8150	Discontinued
0.744	Intermediate Similarity	NPD7074	Phase 3
0.744	Intermediate Similarity	NPD7472	Approved
0.7438	Intermediate Similarity	NPD6801	Discontinued
0.7425	Intermediate Similarity	NPD7228	Approved
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.7397	Intermediate Similarity	NPD9494	Approved
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7391	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1613	Approved
0.7372	Intermediate Similarity	NPD6799	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6798	Discontinued
0.7365	Intermediate Similarity	NPD7473	Discontinued
0.7362	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3455	Phase 2
0.7349	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5403	Approved
0.7333	Intermediate Similarity	NPD7199	Phase 2
0.7303	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8434	Phase 2
0.7226	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5401	Approved
0.7181	Intermediate Similarity	NPD7095	Approved
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD4062	Phase 3
0.7078	Intermediate Similarity	NPD1510	Phase 2
0.7078	Intermediate Similarity	NPD7033	Discontinued
0.7076	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7819	Suspended
0.7066	Intermediate Similarity	NPD5494	Approved
0.7055	Intermediate Similarity	NPD7411	Suspended
0.7051	Intermediate Similarity	NPD1549	Phase 2
0.7047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD9570	Approved
0.703	Intermediate Similarity	NPD5353	Approved
0.7007	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6535	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.6993	Remote Similarity	NPD4340	Discontinued
0.6993	Remote Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD5536	Phase 2
0.6987	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7435	Discontinued
0.697	Remote Similarity	NPD8455	Phase 2
0.6962	Remote Similarity	NPD3750	Approved
0.6954	Remote Similarity	NPD7039	Approved
0.6954	Remote Similarity	NPD6559	Discontinued
0.6954	Remote Similarity	NPD7240	Approved
0.6954	Remote Similarity	NPD7038	Approved
0.6943	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5242	Approved
0.6939	Remote Similarity	NPD1608	Approved
0.6928	Remote Similarity	NPD826	Approved
0.6928	Remote Similarity	NPD825	Approved
0.6928	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD1551	Phase 2
0.6906	Remote Similarity	NPD3022	Approved
0.6906	Remote Similarity	NPD3021	Approved
0.6902	Remote Similarity	NPD6781	Approved
0.6902	Remote Similarity	NPD6778	Approved
0.6902	Remote Similarity	NPD6782	Approved
0.6902	Remote Similarity	NPD6780	Approved
0.6902	Remote Similarity	NPD6777	Approved
0.6902	Remote Similarity	NPD6776	Approved
0.6902	Remote Similarity	NPD6779	Approved
0.6901	Remote Similarity	NPD2629	Approved
0.6894	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7700	Phase 2
0.6885	Remote Similarity	NPD7699	Phase 2
0.6875	Remote Similarity	NPD8313	Approved
0.6875	Remote Similarity	NPD8312	Approved
0.6871	Remote Similarity	NPD1535	Discovery
0.6863	Remote Similarity	NPD6663	Approved
0.6855	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4110	Phase 3
0.6846	Remote Similarity	NPD3225	Approved
0.6845	Remote Similarity	NPD8319	Approved
0.6845	Remote Similarity	NPD3749	Approved
0.6845	Remote Similarity	NPD8320	Phase 1
0.6832	Remote Similarity	NPD4357	Discontinued
0.6829	Remote Similarity	NPD3226	Approved
0.6826	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1481	Phase 2
0.6821	Remote Similarity	NPD5736	Approved
0.6818	Remote Similarity	NPD1240	Approved
0.6815	Remote Similarity	NPD5408	Approved
0.6815	Remote Similarity	NPD5405	Approved
0.6815	Remote Similarity	NPD5404	Approved
0.6815	Remote Similarity	NPD2796	Approved
0.6815	Remote Similarity	NPD5406	Approved
0.6813	Remote Similarity	NPD3887	Approved
0.6813	Remote Similarity	NPD2354	Approved
0.6805	Remote Similarity	NPD919	Approved
0.6802	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7097	Phase 1
0.679	Remote Similarity	NPD3146	Approved
0.679	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2532	Approved
0.679	Remote Similarity	NPD2534	Approved
0.679	Remote Similarity	NPD2533	Approved
0.6786	Remote Similarity	NPD7768	Phase 2
0.6774	Remote Similarity	NPD555	Phase 2
0.6772	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7874	Approved
0.6752	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6273	Approved
0.6744	Remote Similarity	NPD3926	Phase 2
0.6742	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4198	Discontinued
0.6735	Remote Similarity	NPD17	Approved
0.6731	Remote Similarity	NPD6653	Approved
0.6731	Remote Similarity	NPD1607	Approved
0.673	Remote Similarity	NPD5958	Discontinued
0.673	Remote Similarity	NPD4534	Discontinued
0.6727	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7458	Discontinued
0.6725	Remote Similarity	NPD6959	Discontinued
0.6725	Remote Similarity	NPD1247	Approved
0.6712	Remote Similarity	NPD1894	Discontinued
0.6711	Remote Similarity	NPD2861	Phase 2
0.6709	Remote Similarity	NPD2438	Suspended
0.6702	Remote Similarity	NPD7698	Approved
0.6702	Remote Similarity	NPD7697	Approved
0.6702	Remote Similarity	NPD7696	Phase 3
0.669	Remote Similarity	NPD9493	Approved
0.669	Remote Similarity	NPD228	Approved
0.6689	Remote Similarity	NPD1470	Approved
0.6689	Remote Similarity	NPD1203	Approved
0.6689	Remote Similarity	NPD2797	Approved
0.6688	Remote Similarity	NPD3268	Approved
0.6687	Remote Similarity	NPD1652	Phase 2
0.6686	Remote Similarity	NPD7229	Phase 3
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD2982	Phase 2

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