NPASS Compound

Structure

NPC117154 OpenBabel07101718222D 35 39 0 0 1 0 0 0 0 0999 V2000 0.2816 5.2699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7680 2.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3533 2.2958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1689 2.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4506 -2.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -2.6479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7680 4.4273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8481 1.0107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2160 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0867 1.5971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1354 -0.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0676 0.0170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2816 3.5847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6080 1.6704 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0214 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6080 0.3510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1426 1.3617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2160 -0.7020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7625 0.8972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8745 0.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6914 1.8995 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6080 -1.0531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4943 -0.0380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5503 -0.2734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6914 3.5847 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 2.0585 -1.1885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1778 4.4273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6080 -2.0260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0936 -1.1324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7348 0.9312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3009 -0.5820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1778 2.7421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 13 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 12 34 1 0 0 0 0 13 26 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 15 4 1 6 0 0 0 15 21 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 18 28 2 0 0 0 0 19 23 2 0 0 0 0 19 33 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 35 1 6 0 0 0 22 25 2 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 31 1 0 0 0 0 26 29 2 0 0 0 0 26 35 1 0 0 0 0 27 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.19
Volume:	481.996
LogP:	3.867
LogD:	4.303
LogS:	-4.759
# Rotatable Bonds:	5
TPSA:	89.52
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	5.3
Fsp3:	0.481
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.819
MDCK Permeability:	2.131394467141945e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.307
30% Bioavailability (F30%):	0.366

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	91.41532135009766%
Volume Distribution (VD):	1.098
Pgp-substrate:	7.186225891113281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.373
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.981
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.969
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.972
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	7.834
Half-life (T1/2):	0.225

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.851
Drug-inuced Liver Injury (DILI):	0.253
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.506
Maximum Recommended Daily Dose:	0.653
Skin Sensitization:	0.05
Carcinogencity:	0.335
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC117154

Natural Product ID:	NPC117154
*Common Name:**	Interiorin
IUPAC Name:	n.a.
Synonyms:	Interiorin
Standard InCHIKey:	NACPYYYBTUKNNL-YSKMNHBWSA-N
Standard InCHI:	InChI=1S/C27H30O8/c1-7-13(2)26(29)35-21-15(4)14(3)8-16-9-18(28)22(30-5)25(31-6)27(16)11-32-24-20(27)17(21)10-19-23(24)34-12-33-19/h7,9-10,14-15,21H,8,11-12H2,1-6H3/b13-7-/t14-,15-,21-,27+/m1/s1
SMILES:	C/C=C(C(=O)O[C@@H]1[C@H](C)[C@H](C)CC2=CC(=O)C(=C([C@@]32c2c1cc1OCOc1c2OC3)OC)OC)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483434
PubChem CID:	14755542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350139]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8946749]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[533793]
NPT2	Others	Unspecified		Activity	=	13.5	%	PMID[533793]
NPT2	Others	Unspecified		Activity	=	52.0	%	PMID[533793]
NPT2	Others	Unspecified		Activity	=	77.4	%	PMID[533793]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[533793]

☑ 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 NPC117154 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	430
0.1-0.2	1577
0.2-0.3	3862
0.3-0.4	9008
0.4-0.5	9864
0.5-0.6	4506
0.6-0.7	9673
0.7-0.8	3589
0.8-0.85	116
0.85-0.9	56
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9363	High Similarity	NPC42230
0.9241	High Similarity	NPC474948
0.9236	High Similarity	NPC475953
0.92	High Similarity	NPC85141
0.913	High Similarity	NPC474568
0.9122	High Similarity	NPC50696
0.9114	High Similarity	NPC474647
0.9007	High Similarity	NPC198129
0.9007	High Similarity	NPC327352
0.9007	High Similarity	NPC477375
0.9007	High Similarity	NPC252281
0.8947	High Similarity	NPC477376
0.8947	High Similarity	NPC322426
0.8947	High Similarity	NPC477374
0.8903	High Similarity	NPC178195
0.8903	High Similarity	NPC348849
0.8903	High Similarity	NPC312763
0.8903	High Similarity	NPC198461
0.8889	High Similarity	NPC316989
0.8851	High Similarity	NPC278076
0.8808	High Similarity	NPC327651
0.8808	High Similarity	NPC318286
0.88	High Similarity	NPC76415
0.88	High Similarity	NPC218510
0.879	High Similarity	NPC473323
0.8766	High Similarity	NPC475170
0.875	High Similarity	NPC321958
0.875	High Similarity	NPC321696
0.8742	High Similarity	NPC326144
0.8718	High Similarity	NPC16791
0.8718	High Similarity	NPC53669
0.8718	High Similarity	NPC77237
0.8718	High Similarity	NPC297271
0.8718	High Similarity	NPC477377
0.8718	High Similarity	NPC217708
0.8718	High Similarity	NPC308739
0.8718	High Similarity	NPC126405
0.8718	High Similarity	NPC24562
0.871	High Similarity	NPC303519
0.8671	High Similarity	NPC477380
0.8671	High Similarity	NPC29727
0.8654	High Similarity	NPC475229
0.8654	High Similarity	NPC477378
0.8645	High Similarity	NPC473989
0.8625	High Similarity	NPC63061
0.8616	High Similarity	NPC477885
0.8608	High Similarity	NPC476065
0.859	High Similarity	NPC224472
0.8571	High Similarity	NPC258322
0.8571	High Similarity	NPC25496
0.8571	High Similarity	NPC191352
0.8562	High Similarity	NPC325122
0.8544	High Similarity	NPC473425
0.8523	High Similarity	NPC11453
0.8516	High Similarity	NPC316676
0.8516	High Similarity	NPC325720
0.85	High Similarity	NPC475592
0.8471	Intermediate Similarity	NPC475756
0.8467	Intermediate Similarity	NPC166184
0.8418	Intermediate Similarity	NPC471154
0.8411	Intermediate Similarity	NPC178290
0.8408	Intermediate Similarity	NPC477381
0.8405	Intermediate Similarity	NPC61141
0.84	Intermediate Similarity	NPC32189
0.8377	Intermediate Similarity	NPC475000
0.8366	Intermediate Similarity	NPC287124
0.8365	Intermediate Similarity	NPC474606
0.8355	Intermediate Similarity	NPC103448
0.8355	Intermediate Similarity	NPC216434
0.8354	Intermediate Similarity	NPC210642
0.8354	Intermediate Similarity	NPC477379
0.8354	Intermediate Similarity	NPC13985
0.8344	Intermediate Similarity	NPC319749
0.8344	Intermediate Similarity	NPC865
0.8333	Intermediate Similarity	NPC230531
0.8333	Intermediate Similarity	NPC183083
0.8333	Intermediate Similarity	NPC215400
0.8333	Intermediate Similarity	NPC137352
0.8333	Intermediate Similarity	NPC295297
0.8323	Intermediate Similarity	NPC476841
0.8323	Intermediate Similarity	NPC475868
0.8323	Intermediate Similarity	NPC476843
0.8313	Intermediate Similarity	NPC273578
0.8313	Intermediate Similarity	NPC79322
0.8312	Intermediate Similarity	NPC474966
0.8303	Intermediate Similarity	NPC477884
0.8293	Intermediate Similarity	NPC280778
0.8291	Intermediate Similarity	NPC149505
0.8291	Intermediate Similarity	NPC177830
0.828	Intermediate Similarity	NPC40654
0.828	Intermediate Similarity	NPC262804
0.8278	Intermediate Similarity	NPC143895
0.8269	Intermediate Similarity	NPC193779
0.8267	Intermediate Similarity	NPC145769
0.8267	Intermediate Similarity	NPC256776
0.8267	Intermediate Similarity	NPC185680
0.8267	Intermediate Similarity	NPC145722
0.8261	Intermediate Similarity	NPC188962
0.8261	Intermediate Similarity	NPC202249
0.8261	Intermediate Similarity	NPC238834
0.8261	Intermediate Similarity	NPC42871
0.8258	Intermediate Similarity	NPC141569
0.8258	Intermediate Similarity	NPC239254
0.8258	Intermediate Similarity	NPC166884
0.8258	Intermediate Similarity	NPC477701
0.8258	Intermediate Similarity	NPC172171
0.8255	Intermediate Similarity	NPC65183
0.8255	Intermediate Similarity	NPC72046
0.8255	Intermediate Similarity	NPC261812
0.825	Intermediate Similarity	NPC149735
0.825	Intermediate Similarity	NPC474514
0.8247	Intermediate Similarity	NPC151423
0.8247	Intermediate Similarity	NPC46180
0.8247	Intermediate Similarity	NPC472562
0.8247	Intermediate Similarity	NPC80326
0.8247	Intermediate Similarity	NPC474295
0.8247	Intermediate Similarity	NPC40237
0.8242	Intermediate Similarity	NPC475865
0.8228	Intermediate Similarity	NPC474393
0.8228	Intermediate Similarity	NPC474347
0.8224	Intermediate Similarity	NPC20796
0.8224	Intermediate Similarity	NPC14697
0.8212	Intermediate Similarity	NPC148893
0.8212	Intermediate Similarity	NPC73071
0.8212	Intermediate Similarity	NPC49235
0.8212	Intermediate Similarity	NPC25333
0.8205	Intermediate Similarity	NPC477702
0.8205	Intermediate Similarity	NPC474158
0.8205	Intermediate Similarity	NPC232883
0.82	Intermediate Similarity	NPC266848
0.82	Intermediate Similarity	NPC136750
0.8194	Intermediate Similarity	NPC324962
0.8187	Intermediate Similarity	NPC104353
0.8187	Intermediate Similarity	NPC220577
0.8182	Intermediate Similarity	NPC300798
0.8182	Intermediate Similarity	NPC312199
0.8182	Intermediate Similarity	NPC58137
0.8176	Intermediate Similarity	NPC470916
0.8171	Intermediate Similarity	NPC119910
0.8165	Intermediate Similarity	NPC477879
0.816	Intermediate Similarity	NPC19947
0.816	Intermediate Similarity	NPC207584
0.8158	Intermediate Similarity	NPC121651
0.8153	Intermediate Similarity	NPC212890
0.8153	Intermediate Similarity	NPC252286
0.8153	Intermediate Similarity	NPC154971
0.8153	Intermediate Similarity	NPC87295
0.8146	Intermediate Similarity	NPC31530
0.8144	Intermediate Similarity	NPC320471
0.8144	Intermediate Similarity	NPC83049
0.8144	Intermediate Similarity	NPC118162
0.8141	Intermediate Similarity	NPC15743
0.8141	Intermediate Similarity	NPC218841
0.8141	Intermediate Similarity	NPC92693
0.8133	Intermediate Similarity	NPC7744
0.8129	Intermediate Similarity	NPC229172
0.8129	Intermediate Similarity	NPC36531
0.8129	Intermediate Similarity	NPC174522
0.8129	Intermediate Similarity	NPC210354
0.8129	Intermediate Similarity	NPC230538
0.8129	Intermediate Similarity	NPC103637
0.8129	Intermediate Similarity	NPC176586
0.8117	Intermediate Similarity	NPC226547
0.811	Intermediate Similarity	NPC173726
0.811	Intermediate Similarity	NPC241600
0.8107	Intermediate Similarity	NPC477883
0.8101	Intermediate Similarity	NPC80230
0.8101	Intermediate Similarity	NPC304687
0.8101	Intermediate Similarity	NPC101755
0.8101	Intermediate Similarity	NPC104024
0.8101	Intermediate Similarity	NPC65574
0.8098	Intermediate Similarity	NPC32373
0.8098	Intermediate Similarity	NPC237946
0.8095	Intermediate Similarity	NPC311912
0.8092	Intermediate Similarity	NPC189474
0.8092	Intermediate Similarity	NPC474139
0.8092	Intermediate Similarity	NPC240915
0.8089	Intermediate Similarity	NPC205316
0.8089	Intermediate Similarity	NPC180953
0.8084	Intermediate Similarity	NPC222531
0.8077	Intermediate Similarity	NPC474288
0.8075	Intermediate Similarity	NPC470264
0.8075	Intermediate Similarity	NPC302610
0.8067	Intermediate Similarity	NPC192255
0.8063	Intermediate Similarity	NPC24425
0.8061	Intermediate Similarity	NPC96593
0.8061	Intermediate Similarity	NPC474770
0.8059	Intermediate Similarity	NPC178737
0.8052	Intermediate Similarity	NPC113550
0.8052	Intermediate Similarity	NPC201404
0.8052	Intermediate Similarity	NPC290714
0.8052	Intermediate Similarity	NPC53722
0.805	Intermediate Similarity	NPC304821
0.805	Intermediate Similarity	NPC93924
0.8049	Intermediate Similarity	NPC220462
0.8047	Intermediate Similarity	NPC88557
0.8038	Intermediate Similarity	NPC474446
0.8026	Intermediate Similarity	NPC90083
0.8026	Intermediate Similarity	NPC170779
0.8026	Intermediate Similarity	NPC7163

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 NPC117154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	972
0.2-0.3	2125
0.3-0.4	2696
0.4-0.5	1703
0.5-0.6	828
0.6-0.7	433
0.7-0.8	44
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8133	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4965	Approved
0.8098	Intermediate Similarity	NPD4966	Approved
0.8098	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7914	Intermediate Similarity	NPD37	Approved
0.7904	Intermediate Similarity	NPD7199	Phase 2
0.7755	Intermediate Similarity	NPD3705	Approved
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7228	Approved
0.7669	Intermediate Similarity	NPD1653	Approved
0.7605	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD7240	Approved
0.7471	Intermediate Similarity	NPD3818	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.7427	Intermediate Similarity	NPD5494	Approved
0.7365	Intermediate Similarity	NPD6599	Discontinued
0.736	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3882	Suspended
0.7333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7808	Phase 3
0.7251	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3748	Approved
0.7247	Intermediate Similarity	NPD6797	Phase 2
0.7239	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5844	Phase 1
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6799	Approved
0.7207	Intermediate Similarity	NPD7251	Discontinued
0.72	Intermediate Similarity	NPD3926	Phase 2
0.7191	Intermediate Similarity	NPD7074	Phase 3
0.7184	Intermediate Similarity	NPD8127	Discontinued
0.7184	Intermediate Similarity	NPD1247	Approved
0.7178	Intermediate Similarity	NPD6674	Discontinued
0.716	Intermediate Similarity	NPD5763	Approved
0.716	Intermediate Similarity	NPD5762	Approved
0.7158	Intermediate Similarity	NPD6843	Phase 3
0.7158	Intermediate Similarity	NPD6842	Approved
0.7158	Intermediate Similarity	NPD6841	Approved
0.7135	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7054	Approved
0.7135	Intermediate Similarity	NPD7819	Suspended
0.7126	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5090	Approved
0.7118	Intermediate Similarity	NPD5089	Approved
0.7111	Intermediate Similarity	NPD6559	Discontinued
0.711	Intermediate Similarity	NPD7075	Discontinued
0.7095	Intermediate Similarity	NPD7472	Approved
0.7093	Intermediate Similarity	NPD5402	Approved
0.7079	Intermediate Similarity	NPD3751	Discontinued
0.7076	Intermediate Similarity	NPD1934	Approved
0.7076	Intermediate Similarity	NPD6801	Discontinued
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7062	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6166	Phase 2
0.7059	Intermediate Similarity	NPD7028	Phase 2
0.7056	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4585	Approved
0.7035	Intermediate Similarity	NPD1465	Phase 2
0.703	Intermediate Similarity	NPD3750	Approved
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3027	Phase 3
0.7022	Intermediate Similarity	NPD7473	Discontinued
0.7011	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8434	Phase 2
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.6995	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5403	Approved
0.6974	Remote Similarity	NPD5691	Approved
0.6971	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4481	Phase 3
0.6964	Remote Similarity	NPD5401	Approved
0.6951	Remote Similarity	NPD7266	Discontinued
0.6949	Remote Similarity	NPD3787	Discontinued
0.6949	Remote Similarity	NPD6232	Discontinued
0.6944	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7095	Approved
0.6911	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3018	Phase 2
0.6899	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5353	Approved
0.6891	Remote Similarity	NPD5006	Approved
0.6891	Remote Similarity	NPD5005	Approved
0.689	Remote Similarity	NPD2796	Approved
0.6875	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1652	Phase 2
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6863	Remote Similarity	NPD1357	Approved
0.6855	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5124	Phase 1
0.6852	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1933	Approved
0.6842	Remote Similarity	NPD5536	Phase 2
0.6839	Remote Similarity	NPD422	Phase 1
0.6839	Remote Similarity	NPD2801	Approved
0.6835	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4628	Phase 3
0.6802	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5283	Phase 1
0.6795	Remote Similarity	NPD2981	Phase 2
0.6793	Remote Similarity	NPD7549	Discontinued
0.679	Remote Similarity	NPD4140	Approved
0.6788	Remote Similarity	NPD6099	Approved
0.6788	Remote Similarity	NPD4107	Approved
0.6788	Remote Similarity	NPD6100	Approved
0.6784	Remote Similarity	NPD920	Approved
0.6778	Remote Similarity	NPD2403	Approved
0.6774	Remote Similarity	NPD3496	Discontinued
0.6772	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7296	Approved
0.6771	Remote Similarity	NPD4420	Approved
0.677	Remote Similarity	NPD6798	Discontinued
0.6769	Remote Similarity	NPD7680	Approved
0.6766	Remote Similarity	NPD1243	Approved
0.676	Remote Similarity	NPD7229	Phase 3
0.6755	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5585	Approved
0.6752	Remote Similarity	NPD2982	Phase 2
0.6752	Remote Similarity	NPD4749	Approved
0.6752	Remote Similarity	NPD2983	Phase 2
0.675	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4908	Phase 1
0.6731	Remote Similarity	NPD1091	Approved
0.6728	Remote Similarity	NPD8032	Phase 2
0.6725	Remote Similarity	NPD1512	Approved
0.6722	Remote Similarity	NPD5242	Approved
0.671	Remote Similarity	NPD4626	Approved
0.6705	Remote Similarity	NPD2563	Approved
0.6705	Remote Similarity	NPD2560	Approved
0.6687	Remote Similarity	NPD2438	Suspended
0.6686	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD2971	Approved
0.6667	Remote Similarity	NPD1296	Phase 2
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8312	Approved
0.6667	Remote Similarity	NPD4482	Phase 3
0.6667	Remote Similarity	NPD2968	Approved
0.6667	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD6111	Discontinued
0.6667	Remote Similarity	NPD3146	Approved
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6649	Remote Similarity	NPD7685	Pre-registration
0.6648	Remote Similarity	NPD8455	Phase 2
0.6647	Remote Similarity	NPD6005	Phase 3
0.6647	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6004	Phase 3
0.6647	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6002	Phase 3
0.6647	Remote Similarity	NPD1375	Discontinued
0.6647	Remote Similarity	NPD4210	Discontinued
0.6646	Remote Similarity	NPD447	Suspended
0.6646	Remote Similarity	NPD3657	Discovery
0.6646	Remote Similarity	NPD5327	Phase 3
0.6646	Remote Similarity	NPD230	Phase 1
0.6629	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7411	Suspended
0.6628	Remote Similarity	NPD6273	Approved
0.6627	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6233	Phase 2
0.6624	Remote Similarity	NPD1610	Phase 2
0.6622	Remote Similarity	NPD1358	Approved
0.6611	Remote Similarity	NPD6959	Discontinued
0.661	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7458	Discontinued
0.6608	Remote Similarity	NPD1511	Approved
0.6607	Remote Similarity	NPD2424	Discontinued
0.6604	Remote Similarity	NPD8651	Approved
0.6603	Remote Similarity	NPD1778	Approved
0.6601	Remote Similarity	NPD7157	Approved
0.6588	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3620	Phase 2
0.6584	Remote Similarity	NPD2861	Phase 2
0.6571	Remote Similarity	NPD4380	Phase 2
0.657	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3266	Approved
0.6562	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3267	Approved
0.6559	Remote Similarity	NPD6765	Approved
0.6559	Remote Similarity	NPD6764	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