NPASS Compound

Structure

NPC471107 OpenBabel07101718192D 42 45 0 0 1 0 0 0 0 0999 V2000 1.5822 1.7388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6673 2.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4572 3.1410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9647 -1.2781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3072 -2.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0955 -2.8079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5773 -1.2967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5319 -0.9507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6978 -1.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5462 0.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8779 -0.9260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7264 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1617 1.5839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1356 0.1515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7624 1.2490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1412 1.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2771 2.6512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1633 -0.3439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -1.7022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8922 0.0290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4287 1.2312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2502 -0.9083 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5652 -0.9699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4184 0.5435 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5453 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0900 -0.4729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0724 0.5188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2951 -0.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1823 0.2086 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7726 0.5614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5684 0.8343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1112 3.1163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0716 -0.0488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9252 -1.9973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2296 -1.8641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0867 1.4737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1879 1.7456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2628 1.6963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4536 0.2951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8183 -0.7680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2382 0.0537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 28 1 0 0 0 0 7 28 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 29 1 0 0 0 0 14 37 1 0 0 0 0 15 30 1 1 0 0 0 16 31 2 0 0 0 0 16 37 1 0 0 0 0 17 32 2 0 0 0 0 17 38 1 0 0 0 0 18 33 2 0 0 0 0 18 39 1 0 0 0 0 19 34 2 0 0 0 0 19 40 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 38 1 1 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 35 2 0 0 0 0 24 29 1 1 0 0 0 24 41 1 0 0 0 0 25 30 1 6 0 0 0 25 39 1 0 0 0 0 26 29 1 1 0 0 0 26 40 1 0 0 0 0 27 36 2 0 0 0 0 27 41 1 0 0 0 0 28 42 1 0 0 0 0 29 30 1 6 0 0 0 30 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.22
Volume:	574.965
LogP:	3.22
LogD:	1.296
LogS:	-3.783
# Rotatable Bonds:	12
TPSA:	157.8
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	5.926
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.357
MDCK Permeability:	9.821471030591056e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.519
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.644
Plasma Protein Binding (PPB):	40.418861389160156%
Volume Distribution (VD):	1.717
Pgp-substrate:	33.683837890625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.508
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.319
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	3.343
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.336
Carcinogencity:	0.123
Eye Corrosion:	0.033
Eye Irritation:	0.218
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC471107

Natural Product ID:	NPC471107
*Common Name:**	YTJZKJLJHWCAEU-RWHORTGKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YTJZKJLJHWCAEU-RWHORTGKSA-N
Standard InCHI:	InChI=1S/C30H36O12/c1-15-13-21(38-17(3)32)24(41-27(36)20-11-9-8-10-12-20)29(14-37-16(2)31)26(40-19(5)34)23(35)22-25(39-18(4)33)30(15,29)42-28(22,6)7/h8-12,15,21-22,24-26H,13-14H2,1-7H3/t15-,21+,22?,24+,25-,26-,29+,30-/m1/s1
SMILES:	CC(=O)OC[C@]12[C@@H](OC(=O)c3ccccc3)[C@@H](OC(=O)C)C[C@H]([C@@]32OC(C(C(=O)[C@H]1OC(=O)C)[C@H]3OC(=O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2373546
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]

☑ 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
Ki	3
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	Ki	=	5740.0	nM	PMID[485012]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	5740.0	nM	PMID[485013]
NPT35	Others	n.a.		LogP	=	6.1	n.a.	PMID[485013]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	5754.4	nM	PMID[485013]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Imax	=	96.4	%	PMID[485013]

☑ 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 NPC471107 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	380
0.1-0.2	1235
0.2-0.3	2373
0.3-0.4	5140
0.4-0.5	9739
0.5-0.6	10862
0.6-0.7	10621
0.7-0.8	1838
0.8-0.85	259
0.85-0.9	163
0.9-0.95	80
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471100
0.9714	High Similarity	NPC254558
0.9645	High Similarity	NPC471103
0.9645	High Similarity	NPC51602
0.9444	High Similarity	NPC282239
0.9429	High Similarity	NPC127857
0.9379	High Similarity	NPC106895
0.9357	High Similarity	NPC470231
0.9338	High Similarity	NPC291638
0.9338	High Similarity	NPC17877
0.9338	High Similarity	NPC472577
0.9338	High Similarity	NPC195647
0.9338	High Similarity	NPC66761
0.9315	High Similarity	NPC472393
0.931	High Similarity	NPC21410
0.931	High Similarity	NPC473670
0.9265	High Similarity	NPC474608
0.9252	High Similarity	NPC471102
0.9247	High Similarity	NPC217091
0.9236	High Similarity	NPC101043
0.9236	High Similarity	NPC306799
0.9231	High Similarity	NPC81698
0.9231	High Similarity	NPC250046
0.9231	High Similarity	NPC60509
0.9209	High Similarity	NPC477904
0.9209	High Similarity	NPC183270
0.9167	High Similarity	NPC165260
0.9167	High Similarity	NPC112216
0.9167	High Similarity	NPC198455
0.9167	High Similarity	NPC7095
0.9167	High Similarity	NPC161239
0.911	High Similarity	NPC219419
0.9078	High Similarity	NPC182869
0.9071	High Similarity	NPC473758
0.9071	High Similarity	NPC211137
0.9071	High Similarity	NPC473060
0.9071	High Similarity	NPC171207
0.9071	High Similarity	NPC473081
0.9071	High Similarity	NPC90614
0.9071	High Similarity	NPC4341
0.9071	High Similarity	NPC473085
0.9071	High Similarity	NPC200592
0.9071	High Similarity	NPC184747
0.9071	High Similarity	NPC48017
0.9071	High Similarity	NPC473112
0.9071	High Similarity	NPC473613
0.9071	High Similarity	NPC147880
0.9071	High Similarity	NPC476094
0.9071	High Similarity	NPC97667
0.9071	High Similarity	NPC473109
0.9071	High Similarity	NPC43241
0.9065	High Similarity	NPC283375
0.9065	High Similarity	NPC183122
0.9048	High Similarity	NPC228204
0.9048	High Similarity	NPC26033
0.9048	High Similarity	NPC472549
0.9048	High Similarity	NPC259144
0.9048	High Similarity	NPC114357
0.9048	High Similarity	NPC155329
0.9034	High Similarity	NPC473214
0.9034	High Similarity	NPC470245
0.9007	High Similarity	NPC291599
0.9007	High Similarity	NPC27377
0.9007	High Similarity	NPC41481
0.9007	High Similarity	NPC16912
0.9007	High Similarity	NPC472576
0.9007	High Similarity	NPC87448
0.9007	High Similarity	NPC118080
0.9007	High Similarity	NPC97947
0.9	High Similarity	NPC475652
0.9	High Similarity	NPC214550
0.9	High Similarity	NPC210591
0.898	High Similarity	NPC158333
0.898	High Similarity	NPC472022
0.898	High Similarity	NPC77719
0.898	High Similarity	NPC472005
0.898	High Similarity	NPC473414
0.898	High Similarity	NPC265395
0.898	High Similarity	NPC249471
0.898	High Similarity	NPC304876
0.898	High Similarity	NPC1173
0.898	High Similarity	NPC257213
0.898	High Similarity	NPC248265
0.898	High Similarity	NPC256142
0.898	High Similarity	NPC229545
0.898	High Similarity	NPC242262
0.898	High Similarity	NPC11588
0.898	High Similarity	NPC472030
0.898	High Similarity	NPC134685
0.898	High Similarity	NPC237549
0.8973	High Similarity	NPC470153
0.8971	High Similarity	NPC147561
0.8966	High Similarity	NPC473215
0.8966	High Similarity	NPC476975
0.8958	High Similarity	NPC475552
0.8951	High Similarity	NPC80895
0.8951	High Similarity	NPC471912
0.8936	High Similarity	NPC275592
0.8936	High Similarity	NPC100913
0.8919	High Similarity	NPC114410
0.8919	High Similarity	NPC112523
0.8912	High Similarity	NPC472548
0.8912	High Similarity	NPC477905
0.8904	High Similarity	NPC91730
0.8889	High Similarity	NPC277053
0.8889	High Similarity	NPC301946
0.8881	High Similarity	NPC473673
0.8881	High Similarity	NPC477894
0.8881	High Similarity	NPC270498
0.8881	High Similarity	NPC147217
0.8881	High Similarity	NPC475429
0.8881	High Similarity	NPC246480
0.8881	High Similarity	NPC177340
0.8881	High Similarity	NPC163087
0.8881	High Similarity	NPC191082
0.8881	High Similarity	NPC139067
0.8844	High Similarity	NPC197037
0.8836	High Similarity	NPC473403
0.8828	High Similarity	NPC477737
0.8819	High Similarity	NPC25768
0.8819	High Similarity	NPC188865
0.8819	High Similarity	NPC95265
0.8819	High Similarity	NPC95810
0.8819	High Similarity	NPC11685
0.8819	High Similarity	NPC163719
0.8819	High Similarity	NPC472570
0.8819	High Similarity	NPC70716
0.8819	High Similarity	NPC125106
0.8819	High Similarity	NPC51314
0.8819	High Similarity	NPC57628
0.8819	High Similarity	NPC67777
0.8819	High Similarity	NPC470152
0.8819	High Similarity	NPC472573
0.8819	High Similarity	NPC472569
0.8819	High Similarity	NPC241951
0.8819	High Similarity	NPC475759
0.8819	High Similarity	NPC476974
0.8811	High Similarity	NPC472546
0.88	High Similarity	NPC469771
0.8794	High Similarity	NPC184109
0.8792	High Similarity	NPC473632
0.8792	High Similarity	NPC469730
0.8792	High Similarity	NPC473611
0.8792	High Similarity	NPC132599
0.8767	High Similarity	NPC217918
0.8759	High Similarity	NPC96903
0.8759	High Similarity	NPC472575
0.8759	High Similarity	NPC469349
0.8759	High Similarity	NPC158663
0.8759	High Similarity	NPC171525
0.8759	High Similarity	NPC29704
0.8759	High Similarity	NPC470159
0.8759	High Similarity	NPC174982
0.8759	High Similarity	NPC472572
0.8759	High Similarity	NPC177940
0.8759	High Similarity	NPC70403
0.8759	High Similarity	NPC184817
0.8759	High Similarity	NPC471104
0.8759	High Similarity	NPC472568
0.8759	High Similarity	NPC200471
0.8759	High Similarity	NPC476973
0.8759	High Similarity	NPC470157
0.8759	High Similarity	NPC472571
0.8759	High Similarity	NPC473088
0.8742	High Similarity	NPC469399
0.8733	High Similarity	NPC11410
0.8725	High Similarity	NPC469477
0.8725	High Similarity	NPC133430
0.8699	High Similarity	NPC474935
0.8693	High Similarity	NPC55744
0.869	High Similarity	NPC475122
0.8675	High Similarity	NPC469417
0.8671	High Similarity	NPC472547
0.8667	High Similarity	NPC251139
0.8658	High Similarity	NPC469648
0.8658	High Similarity	NPC22571
0.8658	High Similarity	NPC138641
0.8658	High Similarity	NPC469647
0.8658	High Similarity	NPC283875
0.8654	High Similarity	NPC102465
0.8652	High Similarity	NPC477893
0.8639	High Similarity	NPC132652
0.8639	High Similarity	NPC281717
0.8636	High Similarity	NPC66193
0.8609	High Similarity	NPC70344
0.8592	High Similarity	NPC472551
0.8592	High Similarity	NPC472545
0.8581	High Similarity	NPC92293
0.8581	High Similarity	NPC471134
0.8581	High Similarity	NPC270590
0.8581	High Similarity	NPC301556
0.8581	High Similarity	NPC471101
0.8581	High Similarity	NPC266265
0.8581	High Similarity	NPC471493
0.8571	High Similarity	NPC43304
0.8571	High Similarity	NPC477188
0.8571	High Similarity	NPC472394
0.8571	High Similarity	NPC469513
0.8571	High Similarity	NPC477190
0.8552	High Similarity	NPC475135

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 NPC471107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	771
0.2-0.3	1508
0.3-0.4	2958
0.4-0.5	2206
0.5-0.6	1032
0.6-0.7	342
0.7-0.8	34
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8255	Intermediate Similarity	NPD7236	Approved
0.8199	Intermediate Similarity	NPD7799	Discontinued
0.8182	Intermediate Similarity	NPD8407	Phase 2
0.811	Intermediate Similarity	NPD8368	Discontinued
0.8105	Intermediate Similarity	NPD7239	Suspended
0.7976	Intermediate Similarity	NPD8434	Phase 2
0.7882	Intermediate Similarity	NPD8435	Approved
0.7778	Intermediate Similarity	NPD8360	Approved
0.7778	Intermediate Similarity	NPD8361	Approved
0.764	Intermediate Similarity	NPD7058	Phase 2
0.764	Intermediate Similarity	NPD7057	Phase 3
0.7635	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8485	Approved
0.7558	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8150	Discontinued
0.7438	Intermediate Similarity	NPD6599	Discontinued
0.7407	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5494	Approved
0.7386	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6190	Approved
0.7343	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7961	Discontinued
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7256	Intermediate Similarity	NPD3817	Phase 2
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7234	Intermediate Similarity	NPD4198	Discontinued
0.7195	Intermediate Similarity	NPD7819	Suspended
0.717	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD8462	Phase 1
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6232	Discontinued
0.7101	Intermediate Similarity	NPD2182	Approved
0.7091	Intermediate Similarity	NPD5760	Phase 2
0.7091	Intermediate Similarity	NPD5761	Phase 2
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7069	Intermediate Similarity	NPD6765	Approved
0.7069	Intermediate Similarity	NPD6764	Approved
0.7055	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2067	Discontinued
0.7042	Intermediate Similarity	NPD2629	Approved
0.7039	Intermediate Similarity	NPD3764	Approved
0.7024	Intermediate Similarity	NPD919	Approved
0.7019	Intermediate Similarity	NPD2532	Approved
0.7019	Intermediate Similarity	NPD2534	Approved
0.7019	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5844	Phase 1
0.6989	Remote Similarity	NPD7435	Discontinued
0.6974	Remote Similarity	NPD7008	Discontinued
0.6952	Remote Similarity	NPD8320	Phase 1
0.6952	Remote Similarity	NPD8319	Approved
0.6951	Remote Similarity	NPD7458	Discontinued
0.6951	Remote Similarity	NPD3226	Approved
0.695	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2796	Approved
0.6941	Remote Similarity	NPD8127	Discontinued
0.6941	Remote Similarity	NPD1247	Approved
0.6933	Remote Similarity	NPD5403	Approved
0.6928	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD6535	Approved
0.6914	Remote Similarity	NPD5401	Approved
0.691	Remote Similarity	NPD6784	Approved
0.691	Remote Similarity	NPD6785	Approved
0.6909	Remote Similarity	NPD4380	Phase 2
0.6907	Remote Similarity	NPD8404	Phase 2
0.6905	Remote Similarity	NPD4965	Approved
0.6905	Remote Similarity	NPD4967	Phase 2
0.6905	Remote Similarity	NPD4966	Approved
0.6905	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7699	Phase 2
0.6902	Remote Similarity	NPD7700	Phase 2
0.6901	Remote Similarity	NPD6858	Approved
0.6901	Remote Similarity	NPD7094	Approved
0.6892	Remote Similarity	NPD6287	Discontinued
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8166	Discontinued
0.6867	Remote Similarity	NPD7411	Suspended
0.686	Remote Similarity	NPD3926	Phase 2
0.6849	Remote Similarity	NPD7741	Discontinued
0.6845	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3818	Discontinued
0.6839	Remote Similarity	NPD3751	Discontinued
0.6836	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD920	Approved
0.6824	Remote Similarity	NPD6234	Discontinued
0.6821	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6166	Phase 2
0.6821	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD164	Approved
0.681	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5951	Approved
0.6802	Remote Similarity	NPD3787	Discontinued
0.68	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8313	Approved
0.6798	Remote Similarity	NPD8312	Approved
0.6792	Remote Similarity	NPD2346	Discontinued
0.6786	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7874	Approved
0.6771	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6273	Approved
0.6765	Remote Similarity	NPD3749	Approved
0.6763	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6777	Approved
0.6738	Remote Similarity	NPD6778	Approved
0.6738	Remote Similarity	NPD6779	Approved
0.6738	Remote Similarity	NPD6776	Approved
0.6738	Remote Similarity	NPD6780	Approved
0.6738	Remote Similarity	NPD6781	Approved
0.6738	Remote Similarity	NPD6782	Approved
0.6728	Remote Similarity	NPD3887	Approved
0.6726	Remote Similarity	NPD1934	Approved
0.6723	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7497	Discontinued
0.672	Remote Similarity	NPD7697	Approved
0.672	Remote Similarity	NPD7698	Approved
0.672	Remote Similarity	NPD7696	Phase 3
0.6707	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD230	Phase 1
0.6688	Remote Similarity	NPD6355	Discontinued
0.6688	Remote Similarity	NPD6832	Phase 2
0.6687	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2801	Approved
0.6685	Remote Similarity	NPD6559	Discontinued
0.6685	Remote Similarity	NPD7251	Discontinued
0.6684	Remote Similarity	NPD7871	Phase 2
0.6684	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2799	Discontinued
0.6648	Remote Similarity	NPD7228	Approved
0.6648	Remote Similarity	NPD7808	Phase 3
0.6648	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6959	Discontinued
0.6647	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5667	Approved
0.6644	Remote Similarity	NPD5125	Phase 3
0.6644	Remote Similarity	NPD5126	Approved
0.6644	Remote Similarity	NPD3317	Approved
0.6642	Remote Similarity	NPD1238	Approved
0.6629	Remote Similarity	NPD6797	Phase 2
0.6629	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2403	Approved
0.6625	Remote Similarity	NPD2935	Discontinued
0.6625	Remote Similarity	NPD2438	Suspended
0.6623	Remote Similarity	NPD3972	Approved
0.662	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7768	Phase 2
0.6606	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2800	Approved
0.6605	Remote Similarity	NPD1243	Approved
0.6603	Remote Similarity	NPD2313	Discontinued
0.6596	Remote Similarity	NPD8285	Discontinued
0.6592	Remote Similarity	NPD7685	Pre-registration
0.6585	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7701	Phase 2
0.6573	Remote Similarity	NPD7074	Phase 3
0.6568	Remote Similarity	NPD6385	Approved
0.6568	Remote Similarity	NPD6386	Approved
0.6564	Remote Similarity	NPD7003	Approved
0.6564	Remote Similarity	NPD7801	Approved
0.6562	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7305	Phase 1
0.6562	Remote Similarity	NPD1510	Phase 2
0.6561	Remote Similarity	NPD7713	Phase 3
0.6561	Remote Similarity	NPD6233	Phase 2
0.6561	Remote Similarity	NPD6663	Approved
0.6554	Remote Similarity	NPD7610	Discontinued
0.6552	Remote Similarity	NPD7199	Phase 2
0.655	Remote Similarity	NPD5353	Approved
0.6549	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD1549	Phase 2
0.6538	Remote Similarity	NPD7095	Approved
0.6534	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6099	Approved
0.6522	Remote Similarity	NPD6100	Approved
0.6522	Remote Similarity	NPD5405	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