NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	650.18
Volume:	607.489
LogP:	0.271
LogD:	-0.032
LogS:	-3.138
# Rotatable Bonds:	12
TPSA:	262.36
# H-Bond Aceptor:	16
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.076
Synthetic Accessibility Score:	4.691
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.468
MDCK Permeability:	5.635274283122271e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.706
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	94.85939025878906%
Volume Distribution (VD):	0.44
Pgp-substrate:	6.145956516265869%

ADMET: Metabolism

CYP1A2-inhibitor:	0.275
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	1.107
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.245
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.954
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.136
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC476867

Natural Product ID:	NPC476867
*Common Name:**	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-[4-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphenyl]prop-2-enoate
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-[4-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphenyl]prop-2-enoate
Synonyms:
Standard InCHIKey:	HFIRFUKEPOQTLQ-KTFGOVRASA-N
Standard InCHI:	InChI=1S/C30H34O16/c31-12-19-23(36)25(38)28(41)30(44-19)46-22(35)10-4-14-1-6-16(7-2-14)43-29-27(40)26(39)24(37)20(45-29)13-42-21(34)9-5-15-3-8-17(32)18(33)11-15/h1-11,19-20,23-33,36-41H,12-13H2/b9-5+,10-4+/t19-,20-,23-,24-,25+,26+,27-,28-,29-,30+/m1/s1
SMILES:	C1=CC(=CC=C1/C=C/C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181706
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters [CHEMONTID:0003479] O-cinnamoyl 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	=	99.7	%	PMID[26143931]
NPT1	Others	Radical scavenging activity		ED50	=	47	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 NPC476867 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	354
0.1-0.2	1623
0.2-0.3	4157
0.3-0.4	9805
0.4-0.5	8329
0.5-0.6	5998
0.6-0.7	8256
0.7-0.8	3538
0.8-0.85	411
0.85-0.9	154
0.9-0.95	61
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC476868
0.9927	High Similarity	NPC476869
0.9927	High Similarity	NPC476864
0.9927	High Similarity	NPC476866
0.9855	High Similarity	NPC476865
0.9635	High Similarity	NPC186406
0.9577	High Similarity	NPC476871
0.9565	High Similarity	NPC157816
0.9562	High Similarity	NPC202700
0.95	High Similarity	NPC100998
0.95	High Similarity	NPC252292
0.95	High Similarity	NPC476382
0.95	High Similarity	NPC34587
0.95	High Similarity	NPC34927
0.9496	High Similarity	NPC478239
0.9429	High Similarity	NPC292443
0.9429	High Similarity	NPC232228
0.9371	High Similarity	NPC259347
0.9371	High Similarity	NPC476386
0.9371	High Similarity	NPC470933
0.9371	High Similarity	NPC94871
0.9371	High Similarity	NPC476398
0.9371	High Similarity	NPC471062
0.9371	High Similarity	NPC473427
0.9371	High Similarity	NPC306890
0.9366	High Similarity	NPC232992
0.9362	High Similarity	NPC262182
0.9362	High Similarity	NPC83743
0.9362	High Similarity	NPC287615
0.9362	High Similarity	NPC216819
0.9353	High Similarity	NPC134405
0.9353	High Similarity	NPC476385
0.9348	High Similarity	NPC205195
0.9348	High Similarity	NPC100389
0.9343	High Similarity	NPC186418
0.9306	High Similarity	NPC470934
0.9306	High Similarity	NPC257970
0.9306	High Similarity	NPC470927
0.9306	High Similarity	NPC188393
0.9301	High Similarity	NPC80732
0.9301	High Similarity	NPC192763
0.9301	High Similarity	NPC300262
0.9301	High Similarity	NPC261122
0.9301	High Similarity	NPC201148
0.9301	High Similarity	NPC215095
0.9301	High Similarity	NPC210611
0.9301	High Similarity	NPC3460
0.9301	High Similarity	NPC28651
0.9301	High Similarity	NPC199311
0.9296	High Similarity	NPC199928
0.9291	High Similarity	NPC110063
0.9286	High Similarity	NPC140502
0.9275	High Similarity	NPC260425
0.9275	High Similarity	NPC78363
0.927	High Similarity	NPC476870
0.9236	High Similarity	NPC106138
0.9214	High Similarity	NPC476377
0.9214	High Similarity	NPC47471
0.9209	High Similarity	NPC472350
0.9209	High Similarity	NPC89105
0.9209	High Similarity	NPC64141
0.9209	High Similarity	NPC476383
0.9209	High Similarity	NPC197316
0.9209	High Similarity	NPC81515
0.9209	High Similarity	NPC68092
0.9203	High Similarity	NPC37468
0.9203	High Similarity	NPC157554
0.9167	High Similarity	NPC478237
0.9149	High Similarity	NPC222433
0.9149	High Similarity	NPC265648
0.9143	High Similarity	NPC473799
0.9143	High Similarity	NPC106944
0.9143	High Similarity	NPC475530
0.9137	High Similarity	NPC476376
0.911	High Similarity	NPC7145
0.911	High Similarity	NPC143480
0.911	High Similarity	NPC85192
0.911	High Similarity	NPC125823
0.9103	High Similarity	NPC283839
0.9103	High Similarity	NPC90896
0.9085	High Similarity	NPC476378
0.9085	High Similarity	NPC105005
0.9085	High Similarity	NPC205864
0.9085	High Similarity	NPC175214
0.9085	High Similarity	NPC76406
0.9085	High Similarity	NPC112
0.9085	High Similarity	NPC119537
0.9085	High Similarity	NPC264632
0.9085	High Similarity	NPC476380
0.9085	High Similarity	NPC476381
0.9085	High Similarity	NPC269141
0.9085	High Similarity	NPC476384
0.9085	High Similarity	NPC247032
0.9085	High Similarity	NPC298257
0.9085	High Similarity	NPC476375
0.9085	High Similarity	NPC96795
0.9085	High Similarity	NPC476397
0.9071	High Similarity	NPC226005
0.9065	High Similarity	NPC471665
0.9065	High Similarity	NPC471664
0.9058	High Similarity	NPC886
0.9058	High Similarity	NPC34293
0.9058	High Similarity	NPC287597
0.9051	High Similarity	NPC473285
0.9048	High Similarity	NPC289967
0.9048	High Similarity	NPC472611
0.9048	High Similarity	NPC472612
0.9021	High Similarity	NPC141455
0.9021	High Similarity	NPC296954
0.9021	High Similarity	NPC64195
0.9021	High Similarity	NPC196063
0.9021	High Similarity	NPC300894
0.9014	High Similarity	NPC473792
0.9014	High Similarity	NPC473873
0.9014	High Similarity	NPC145319
0.9	High Similarity	NPC138738
0.9	High Similarity	NPC126206
0.9	High Similarity	NPC470413
0.8971	High Similarity	NPC477294
0.8971	High Similarity	NPC477293
0.8971	High Similarity	NPC229784
0.8936	High Similarity	NPC321184
0.8936	High Similarity	NPC321638
0.8936	High Similarity	NPC328273
0.8936	High Similarity	NPC171134
0.8933	High Similarity	NPC11411
0.8929	High Similarity	NPC242028
0.8929	High Similarity	NPC166180
0.8929	High Similarity	NPC203230
0.8921	High Similarity	NPC471883
0.8919	High Similarity	NPC176186
0.8919	High Similarity	NPC53587
0.8919	High Similarity	NPC478268
0.8919	High Similarity	NPC169404
0.8904	High Similarity	NPC116229
0.8897	High Similarity	NPC229505
0.8897	High Similarity	NPC232880
0.8889	High Similarity	NPC297342
0.8865	High Similarity	NPC124149
0.8865	High Similarity	NPC65530
0.8865	High Similarity	NPC59324
0.8859	High Similarity	NPC157898
0.8859	High Similarity	NPC150442
0.8857	High Similarity	NPC55040
0.8844	High Similarity	NPC478242
0.8844	High Similarity	NPC111785
0.8841	High Similarity	NPC138777
0.8841	High Similarity	NPC246869
0.8841	High Similarity	NPC225384
0.8841	High Similarity	NPC219677
0.8836	High Similarity	NPC52740
0.8836	High Similarity	NPC41844
0.8828	High Similarity	NPC138915
0.8828	High Similarity	NPC473909
0.8828	High Similarity	NPC143120
0.8828	High Similarity	NPC274960
0.8824	High Similarity	NPC476873
0.8824	High Similarity	NPC7191
0.8824	High Similarity	NPC149873
0.8819	High Similarity	NPC113680
0.8819	High Similarity	NPC278961
0.8819	High Similarity	NPC40305
0.8816	High Similarity	NPC478269
0.8803	High Similarity	NPC212770
0.8803	High Similarity	NPC98777
0.88	High Similarity	NPC191046
0.88	High Similarity	NPC327032
0.88	High Similarity	NPC194095
0.8794	High Similarity	NPC40664
0.8794	High Similarity	NPC165482
0.8794	High Similarity	NPC197723
0.8794	High Similarity	NPC138350
0.8794	High Similarity	NPC3293
0.8794	High Similarity	NPC199459
0.8794	High Similarity	NPC52277
0.8794	High Similarity	NPC177035
0.8792	High Similarity	NPC215060
0.8792	High Similarity	NPC476352
0.8786	High Similarity	NPC130496
0.8786	High Similarity	NPC187194
0.8786	High Similarity	NPC35731
0.8786	High Similarity	NPC476411
0.8786	High Similarity	NPC135127
0.8786	High Similarity	NPC188555
0.8777	High Similarity	NPC254275
0.8777	High Similarity	NPC473924
0.8776	High Similarity	NPC93924
0.8776	High Similarity	NPC280945
0.8759	High Similarity	NPC76176
0.8759	High Similarity	NPC138227
0.8759	High Similarity	NPC469313
0.8759	High Similarity	NPC168579
0.875	High Similarity	NPC133984
0.875	High Similarity	NPC469559
0.8733	High Similarity	NPC246893
0.8725	High Similarity	NPC213197
0.8723	High Similarity	NPC214729
0.8723	High Similarity	NPC185778
0.8723	High Similarity	NPC238243
0.8716	High Similarity	NPC212670

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 NPC476867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	861
0.2-0.3	1835
0.3-0.4	2919
0.4-0.5	1776
0.5-0.6	997
0.6-0.7	423
0.7-0.8	47
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9209	High Similarity	NPD7266	Discontinued
0.8716	High Similarity	NPD1653	Approved
0.821	Intermediate Similarity	NPD7472	Approved
0.8148	Intermediate Similarity	NPD7054	Approved
0.811	Intermediate Similarity	NPD7251	Discontinued
0.8098	Intermediate Similarity	NPD7074	Phase 3
0.8049	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD8455	Phase 2
0.7952	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7808	Phase 3
0.7866	Intermediate Similarity	NPD7228	Approved
0.7866	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD1091	Approved
0.7829	Intermediate Similarity	NPD6190	Approved
0.7812	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD3027	Phase 3
0.7746	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6674	Discontinued
0.7692	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD8313	Approved
0.7655	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.7471	Intermediate Similarity	NPD7240	Approved
0.7453	Intermediate Similarity	NPD37	Approved
0.7453	Intermediate Similarity	NPD1934	Approved
0.7423	Intermediate Similarity	NPD4965	Approved
0.7423	Intermediate Similarity	NPD4967	Phase 2
0.7423	Intermediate Similarity	NPD4966	Approved
0.7419	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD1465	Phase 2
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1357	Approved
0.7368	Intermediate Similarity	NPD7097	Phase 1
0.7351	Intermediate Similarity	NPD4340	Discontinued
0.7349	Intermediate Similarity	NPD7199	Phase 2
0.7297	Intermediate Similarity	NPD2861	Phase 2
0.7294	Intermediate Similarity	NPD5844	Phase 1
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7256	Intermediate Similarity	NPD3817	Phase 2
0.7256	Intermediate Similarity	NPD5402	Approved
0.7254	Intermediate Similarity	NPD5536	Phase 2
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD8127	Discontinued
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7241	Intermediate Similarity	NPD3705	Approved
0.7222	Intermediate Similarity	NPD4380	Phase 2
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7215	Intermediate Similarity	NPD5058	Phase 3
0.72	Intermediate Similarity	NPD7095	Approved
0.7195	Intermediate Similarity	NPD2801	Approved
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD5403	Approved
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7124	Intermediate Similarity	NPD1933	Approved
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7108	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD3225	Approved
0.7095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1512	Approved
0.7078	Intermediate Similarity	NPD6653	Approved
0.7071	Intermediate Similarity	NPD228	Approved
0.7055	Intermediate Similarity	NPD3496	Discontinued
0.7049	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4536	Approved
0.7032	Intermediate Similarity	NPD4538	Approved
0.7027	Intermediate Similarity	NPD2982	Phase 2
0.7027	Intermediate Similarity	NPD2983	Phase 2
0.7025	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7843	Approved
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5401	Approved
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7007	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6994	Remote Similarity	NPD3686	Approved
0.6994	Remote Similarity	NPD3687	Approved
0.6993	Remote Similarity	NPD7157	Approved
0.6989	Remote Similarity	NPD7680	Approved
0.6988	Remote Similarity	NPD2977	Approved
0.6988	Remote Similarity	NPD7819	Suspended
0.6988	Remote Similarity	NPD2978	Approved
0.6987	Remote Similarity	NPD5960	Phase 3
0.6987	Remote Similarity	NPD5588	Approved
0.6981	Remote Similarity	NPD8166	Discontinued
0.6981	Remote Similarity	NPD3750	Approved
0.6975	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1548	Phase 1
0.6959	Remote Similarity	NPD2981	Phase 2
0.6957	Remote Similarity	NPD3134	Approved
0.6954	Remote Similarity	NPD9494	Approved
0.6948	Remote Similarity	NPD1558	Phase 1
0.6932	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD6801	Discontinued
0.6927	Remote Similarity	NPD6841	Approved
0.6927	Remote Similarity	NPD6843	Phase 3
0.6927	Remote Similarity	NPD6842	Approved
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD447	Suspended
0.6901	Remote Similarity	NPD5535	Approved
0.6883	Remote Similarity	NPD4062	Phase 3
0.6882	Remote Similarity	NPD5494	Approved
0.6879	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7039	Approved
0.6875	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7038	Approved
0.6875	Remote Similarity	NPD4110	Phase 3
0.6867	Remote Similarity	NPD7411	Suspended
0.6857	Remote Similarity	NPD2684	Approved
0.6855	Remote Similarity	NPD1549	Phase 2
0.6853	Remote Similarity	NPD5283	Phase 1
0.6852	Remote Similarity	NPD4357	Discontinued
0.6852	Remote Similarity	NPD6799	Approved
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7458	Discontinued
0.6842	Remote Similarity	NPD3018	Phase 2
0.6839	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3620	Phase 2
0.6839	Remote Similarity	NPD4140	Approved
0.6835	Remote Similarity	NPD2935	Discontinued
0.6835	Remote Similarity	NPD968	Approved
0.6835	Remote Similarity	NPD1551	Phase 2
0.6826	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3536	Discontinued
0.6806	Remote Similarity	NPD8151	Discontinued
0.6805	Remote Similarity	NPD7768	Phase 2
0.6803	Remote Similarity	NPD5585	Approved
0.6802	Remote Similarity	NPD6232	Discontinued
0.6792	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD290	Approved
0.6782	Remote Similarity	NPD7473	Discontinued
0.6779	Remote Similarity	NPD1535	Discovery
0.6768	Remote Similarity	NPD6273	Approved
0.6766	Remote Similarity	NPD6385	Approved
0.6766	Remote Similarity	NPD6386	Approved
0.676	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6671	Approved
0.6757	Remote Similarity	NPD1778	Approved
0.6757	Remote Similarity	NPD5846	Approved
0.6757	Remote Similarity	NPD6516	Phase 2
0.6755	Remote Similarity	NPD8651	Approved
0.6752	Remote Similarity	NPD2492	Phase 1
0.675	Remote Similarity	NPD2424	Discontinued
0.6747	Remote Similarity	NPD3455	Phase 2
0.6746	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7783	Phase 2
0.6736	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1894	Discontinued
0.6733	Remote Similarity	NPD1481	Phase 2
0.6733	Remote Similarity	NPD1608	Approved
0.673	Remote Similarity	NPD6032	Approved
0.6727	Remote Similarity	NPD2122	Discontinued
0.672	Remote Similarity	NPD7435	Discontinued
0.6713	Remote Similarity	NPD969	Suspended
0.6711	Remote Similarity	NPD2797	Approved
0.6711	Remote Similarity	NPD1203	Approved
0.671	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3060	Approved
0.6707	Remote Similarity	NPD4123	Phase 3
0.669	Remote Similarity	NPD3022	Approved
0.669	Remote Similarity	NPD3021	Approved
0.6688	Remote Similarity	NPD6832	Phase 2
0.6688	Remote Similarity	NPD5735	Approved
0.6687	Remote Similarity	NPD1375	Discontinued
0.6687	Remote Similarity	NPD7440	Discontinued
0.6685	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	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