NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	666.18
Volume:	616.279
LogP:	0.067
LogD:	-0.063
LogS:	-2.303
# Rotatable Bonds:	12
TPSA:	282.59
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.072
Synthetic Accessibility Score:	4.799
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.737
MDCK Permeability:	5.663963020197116e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.96
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	97.84185028076172%
Volume Distribution (VD):	0.446
Pgp-substrate:	4.510593414306641%

ADMET: Metabolism

CYP1A2-inhibitor:	0.197
CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	1.133
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.154
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.96
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC476868

Natural Product ID:	NPC476868
*Common Name:**	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-[(E)-3-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-enyl]phenoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-[(E)-3-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-enyl]phenoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	QZBUECAZYHVZBH-SKXWEYSTSA-N
Standard InCHI:	InChI=1S/C30H34O17/c31-11-19-23(37)25(39)28(42)30(45-19)47-22(36)8-4-14-2-6-16(33)18(10-14)44-29-27(41)26(40)24(38)20(46-29)12-43-21(35)7-3-13-1-5-15(32)17(34)9-13/h1-10,19-20,23-34,37-42H,11-12H2/b7-3+,8-4+/t19-,20-,23-,24-,25+,26+,27-,28-,29-,30+/m1/s1
SMILES:	C1=CC(=C(C=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C=CC(=C3)/C=C/C(=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181707
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0003003] Hydroxycinnamic acid glycosides

*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
NPO33548	Clematis tashiroi	Species	Ranunculaceae	Eukaryota	aerial parts	Heping District, Taichung City, Taiwan	2012-AUG	PMID[26143931]

☑ 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
ED50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	99.4	%	PMID[26143931]
NPT1	Others	Radical scavenging activity		ED50	=	39.9	nM	PMID[26143931]

☑ 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 NPC476868 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	356
0.1-0.2	1658
0.2-0.3	4204
0.3-0.4	9992
0.4-0.5	8211
0.5-0.6	5968
0.6-0.7	8011
0.7-0.8	3627
0.8-0.85	435
0.85-0.9	164
0.9-0.95	60
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476866
1.0	High Similarity	NPC476864
1.0	High Similarity	NPC476869
0.9928	High Similarity	NPC476865
0.9927	High Similarity	NPC476867
0.9648	High Similarity	NPC476871
0.9638	High Similarity	NPC157816
0.9635	High Similarity	NPC202700
0.9571	High Similarity	NPC34927
0.9571	High Similarity	NPC100998
0.9571	High Similarity	NPC476382
0.9571	High Similarity	NPC252292
0.9571	High Similarity	NPC34587
0.9568	High Similarity	NPC478239
0.9565	High Similarity	NPC186406
0.95	High Similarity	NPC232228
0.9441	High Similarity	NPC306890
0.9441	High Similarity	NPC476398
0.9441	High Similarity	NPC476386
0.9441	High Similarity	NPC470933
0.9441	High Similarity	NPC94871
0.9441	High Similarity	NPC471062
0.9441	High Similarity	NPC473427
0.9441	High Similarity	NPC259347
0.9437	High Similarity	NPC232992
0.9433	High Similarity	NPC287615
0.9433	High Similarity	NPC216819
0.9433	High Similarity	NPC83743
0.9433	High Similarity	NPC262182
0.942	High Similarity	NPC100389
0.9416	High Similarity	NPC186418
0.9375	High Similarity	NPC470927
0.9375	High Similarity	NPC188393
0.9375	High Similarity	NPC470934
0.9375	High Similarity	NPC257970
0.9371	High Similarity	NPC215095
0.9371	High Similarity	NPC261122
0.9371	High Similarity	NPC28651
0.9371	High Similarity	NPC3460
0.9371	High Similarity	NPC199311
0.9371	High Similarity	NPC80732
0.9371	High Similarity	NPC300262
0.9371	High Similarity	NPC201148
0.9371	High Similarity	NPC192763
0.9371	High Similarity	NPC210611
0.9366	High Similarity	NPC199928
0.9362	High Similarity	NPC292443
0.9362	High Similarity	NPC110063
0.9357	High Similarity	NPC140502
0.9306	High Similarity	NPC106138
0.9286	High Similarity	NPC134405
0.9286	High Similarity	NPC476385
0.9281	High Similarity	NPC205195
0.9275	High Similarity	NPC157554
0.9275	High Similarity	NPC37468
0.9236	High Similarity	NPC478237
0.9214	High Similarity	NPC106944
0.9209	High Similarity	NPC260425
0.9209	High Similarity	NPC78363
0.9203	High Similarity	NPC476870
0.9178	High Similarity	NPC85192
0.9178	High Similarity	NPC125823
0.9178	High Similarity	NPC143480
0.9178	High Similarity	NPC7145
0.9172	High Similarity	NPC90896
0.9172	High Similarity	NPC283839
0.9149	High Similarity	NPC476377
0.9149	High Similarity	NPC47471
0.9143	High Similarity	NPC64141
0.9143	High Similarity	NPC81515
0.9143	High Similarity	NPC89105
0.9143	High Similarity	NPC226005
0.9143	High Similarity	NPC472350
0.9143	High Similarity	NPC476383
0.9143	High Similarity	NPC197316
0.9143	High Similarity	NPC68092
0.9137	High Similarity	NPC471664
0.9137	High Similarity	NPC471665
0.9116	High Similarity	NPC472612
0.9116	High Similarity	NPC289967
0.9116	High Similarity	NPC472611
0.9085	High Similarity	NPC222433
0.9085	High Similarity	NPC473873
0.9085	High Similarity	NPC473792
0.9085	High Similarity	NPC265648
0.9078	High Similarity	NPC475530
0.9078	High Similarity	NPC473799
0.9071	High Similarity	NPC138738
0.9071	High Similarity	NPC476376
0.9071	High Similarity	NPC126206
0.9071	High Similarity	NPC470413
0.9021	High Similarity	NPC476397
0.9021	High Similarity	NPC112
0.9021	High Similarity	NPC476378
0.9021	High Similarity	NPC205864
0.9021	High Similarity	NPC476380
0.9021	High Similarity	NPC269141
0.9021	High Similarity	NPC76406
0.9021	High Similarity	NPC175214
0.9021	High Similarity	NPC476381
0.9021	High Similarity	NPC264632
0.9021	High Similarity	NPC119537
0.9021	High Similarity	NPC247032
0.9021	High Similarity	NPC96795
0.9021	High Similarity	NPC476384
0.9021	High Similarity	NPC476375
0.9021	High Similarity	NPC298257
0.9021	High Similarity	NPC105005
0.9	High Similarity	NPC11411
0.8993	High Similarity	NPC886
0.8993	High Similarity	NPC287597
0.8993	High Similarity	NPC34293
0.8986	High Similarity	NPC478268
0.8986	High Similarity	NPC473285
0.8973	High Similarity	NPC116229
0.8958	High Similarity	NPC300894
0.8958	High Similarity	NPC141455
0.8958	High Similarity	NPC196063
0.8958	High Similarity	NPC296954
0.8958	High Similarity	NPC297342
0.8958	High Similarity	NPC64195
0.8951	High Similarity	NPC145319
0.8936	High Similarity	NPC65530
0.8936	High Similarity	NPC59324
0.8929	High Similarity	NPC55040
0.8926	High Similarity	NPC150442
0.8912	High Similarity	NPC478242
0.8912	High Similarity	NPC111785
0.8905	High Similarity	NPC229784
0.8905	High Similarity	NPC477293
0.8905	High Similarity	NPC477294
0.8904	High Similarity	NPC41844
0.8904	High Similarity	NPC52740
0.8897	High Similarity	NPC473909
0.8897	High Similarity	NPC274960
0.8897	High Similarity	NPC143120
0.8889	High Similarity	NPC7191
0.8889	High Similarity	NPC149873
0.8889	High Similarity	NPC113680
0.8889	High Similarity	NPC278961
0.8882	High Similarity	NPC478269
0.8873	High Similarity	NPC321184
0.8873	High Similarity	NPC212770
0.8873	High Similarity	NPC328273
0.8873	High Similarity	NPC321638
0.8873	High Similarity	NPC171134
0.8873	High Similarity	NPC98777
0.8867	High Similarity	NPC191046
0.8867	High Similarity	NPC194095
0.8867	High Similarity	NPC327032
0.8865	High Similarity	NPC203230
0.8865	High Similarity	NPC177035
0.8865	High Similarity	NPC52277
0.8865	High Similarity	NPC199459
0.8865	High Similarity	NPC242028
0.8865	High Similarity	NPC166180
0.8859	High Similarity	NPC215060
0.8859	High Similarity	NPC176186
0.8859	High Similarity	NPC476352
0.8859	High Similarity	NPC169404
0.8859	High Similarity	NPC53587
0.8857	High Similarity	NPC471883
0.8857	High Similarity	NPC35731
0.8857	High Similarity	NPC135127
0.8857	High Similarity	NPC476411
0.8857	High Similarity	NPC187194
0.8844	High Similarity	NPC93924
0.8836	High Similarity	NPC229505
0.8832	High Similarity	NPC232880
0.8819	High Similarity	NPC469559
0.8816	High Similarity	NPC133984
0.8803	High Similarity	NPC124149
0.88	High Similarity	NPC246893
0.88	High Similarity	NPC157898
0.8794	High Similarity	NPC214729
0.8792	High Similarity	NPC213197
0.8784	High Similarity	NPC212670
0.8784	High Similarity	NPC313334
0.8784	High Similarity	NPC206264
0.8777	High Similarity	NPC9912
0.8777	High Similarity	NPC246869
0.8777	High Similarity	NPC138777
0.8777	High Similarity	NPC225384
0.8777	High Similarity	NPC219677
0.8774	High Similarity	NPC227297
0.8768	High Similarity	NPC307110
0.8768	High Similarity	NPC248355
0.8767	High Similarity	NPC138915
0.8766	High Similarity	NPC478267
0.8759	High Similarity	NPC476873
0.8759	High Similarity	NPC46092
0.8759	High Similarity	NPC185307
0.8759	High Similarity	NPC40305
0.8759	High Similarity	NPC470950
0.875	High Similarity	NPC478266
0.875	High Similarity	NPC471405
0.875	High Similarity	NPC228357
0.875	High Similarity	NPC469661
0.8733	High Similarity	NPC36130
0.8733	High Similarity	NPC134905

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 NPC476868 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	868
0.2-0.3	1864
0.3-0.4	2919
0.4-0.5	1769
0.5-0.6	977
0.6-0.7	408
0.7-0.8	49
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD7266	Discontinued
0.8784	High Similarity	NPD1653	Approved
0.8272	Intermediate Similarity	NPD7472	Approved
0.821	Intermediate Similarity	NPD7054	Approved
0.816	Intermediate Similarity	NPD7074	Phase 3
0.8061	Intermediate Similarity	NPD7251	Discontinued
0.8061	Intermediate Similarity	NPD7685	Pre-registration
0.8012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7945	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7927	Intermediate Similarity	NPD7228	Approved
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD8455	Phase 2
0.7862	Intermediate Similarity	NPD3027	Phase 3
0.7817	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1091	Approved
0.7778	Intermediate Similarity	NPD6190	Approved
0.7764	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6674	Discontinued
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD8313	Approved
0.7607	Intermediate Similarity	NPD6234	Discontinued
0.7603	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6166	Phase 2
0.759	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7240	Approved
0.7516	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4965	Approved
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7465	Intermediate Similarity	NPD1357	Approved
0.7456	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6559	Discontinued
0.741	Intermediate Similarity	NPD7199	Phase 2
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7362	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5844	Phase 1
0.7324	Intermediate Similarity	NPD5536	Phase 2
0.732	Intermediate Similarity	NPD7097	Phase 1
0.7317	Intermediate Similarity	NPD3817	Phase 2
0.7312	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3705	Approved
0.7305	Intermediate Similarity	NPD8127	Discontinued
0.7303	Intermediate Similarity	NPD4340	Discontinued
0.7256	Intermediate Similarity	NPD2801	Approved
0.7248	Intermediate Similarity	NPD2861	Phase 2
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7232	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7075	Discontinued
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD1652	Phase 2
0.719	Intermediate Similarity	NPD1933	Approved
0.7178	Intermediate Similarity	NPD4380	Phase 2
0.7171	Intermediate Similarity	NPD6233	Phase 2
0.717	Intermediate Similarity	NPD5058	Phase 3
0.7169	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD228	Approved
0.7125	Intermediate Similarity	NPD1511	Approved
0.7104	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1358	Approved
0.7099	Intermediate Similarity	NPD5403	Approved
0.7095	Intermediate Similarity	NPD2983	Phase 2
0.7095	Intermediate Similarity	NPD2982	Phase 2
0.7093	Intermediate Similarity	NPD3751	Discontinued
0.7086	Intermediate Similarity	NPD4908	Phase 1
0.7078	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD230	Phase 1
0.7056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3686	Approved
0.7055	Intermediate Similarity	NPD3687	Approved
0.7048	Intermediate Similarity	NPD2978	Approved
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2977	Approved
0.7047	Intermediate Similarity	NPD3225	Approved
0.7043	Intermediate Similarity	NPD7680	Approved
0.7037	Intermediate Similarity	NPD1512	Approved
0.7032	Intermediate Similarity	NPD6653	Approved
0.7027	Intermediate Similarity	NPD2981	Phase 2
0.702	Intermediate Similarity	NPD9494	Approved
0.7013	Intermediate Similarity	NPD1558	Phase 1
0.7007	Intermediate Similarity	NPD3496	Discontinued
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7549	Discontinued
0.6987	Remote Similarity	NPD4538	Approved
0.6987	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4536	Approved
0.6983	Remote Similarity	NPD6842	Approved
0.6983	Remote Similarity	NPD6841	Approved
0.6983	Remote Similarity	NPD6843	Phase 3
0.6981	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5401	Approved
0.6972	Remote Similarity	NPD7843	Approved
0.6968	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD447	Suspended
0.6962	Remote Similarity	NPD5762	Approved
0.6962	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD1610	Phase 2
0.6959	Remote Similarity	NPD422	Phase 1
0.6959	Remote Similarity	NPD3787	Discontinued
0.6946	Remote Similarity	NPD7819	Suspended
0.6944	Remote Similarity	NPD7157	Approved
0.6943	Remote Similarity	NPD5588	Approved
0.6943	Remote Similarity	NPD5960	Phase 3
0.6941	Remote Similarity	NPD5494	Approved
0.6937	Remote Similarity	NPD3750	Approved
0.6937	Remote Similarity	NPD8166	Discontinued
0.6937	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4110	Phase 3
0.6933	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7038	Approved
0.6932	Remote Similarity	NPD7039	Approved
0.6923	Remote Similarity	NPD5283	Phase 1
0.6918	Remote Similarity	NPD1548	Phase 1
0.6914	Remote Similarity	NPD4357	Discontinued
0.6908	Remote Similarity	NPD3018	Phase 2
0.6906	Remote Similarity	NPD3134	Approved
0.6903	Remote Similarity	NPD3620	Phase 2
0.6903	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6801	Discontinued
0.6886	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6232	Discontinued
0.6853	Remote Similarity	NPD5535	Approved
0.6839	Remote Similarity	NPD7473	Discontinued
0.6839	Remote Similarity	NPD4062	Phase 3
0.6835	Remote Similarity	NPD7033	Discontinued
0.6832	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7411	Suspended
0.6826	Remote Similarity	NPD6385	Approved
0.6826	Remote Similarity	NPD6386	Approved
0.6816	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2492	Phase 1
0.6813	Remote Similarity	NPD1549	Phase 2
0.681	Remote Similarity	NPD6799	Approved
0.6809	Remote Similarity	NPD2684	Approved
0.6807	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7458	Discontinued
0.6795	Remote Similarity	NPD4140	Approved
0.6792	Remote Similarity	NPD1551	Phase 2
0.6792	Remote Similarity	NPD2935	Discontinued
0.6788	Remote Similarity	NPD2122	Discontinued
0.6786	Remote Similarity	NPD968	Approved
0.6771	Remote Similarity	NPD8151	Discontinued
0.677	Remote Similarity	NPD3060	Approved
0.6768	Remote Similarity	NPD3536	Discontinued
0.6768	Remote Similarity	NPD4123	Phase 3
0.6765	Remote Similarity	NPD7768	Phase 2
0.6757	Remote Similarity	NPD5585	Approved
0.675	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1375	Discontinued
0.675	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD291	Approved
0.6738	Remote Similarity	NPD290	Approved
0.6733	Remote Similarity	NPD1535	Discovery
0.6727	Remote Similarity	NPD6273	Approved
0.6725	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6671	Approved
0.6711	Remote Similarity	NPD6516	Phase 2
0.6711	Remote Similarity	NPD8651	Approved
0.6711	Remote Similarity	NPD1778	Approved
0.6711	Remote Similarity	NPD5846	Approved
0.6708	Remote Similarity	NPD2424	Discontinued
0.6707	Remote Similarity	NPD3455	Phase 2
0.6706	Remote Similarity	NPD5353	Approved
0.6706	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7783	Phase 2
0.6701	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1608	Approved
0.6689	Remote Similarity	NPD1894	Discontinued
0.6689	Remote Similarity	NPD1481	Phase 2
0.6687	Remote Similarity	NPD6032	Approved
0.6684	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD4675	Approved
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4162	Approved
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD4678	Approved
0.6667	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD969	Suspended

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