NPASS Compound

Structure

NPC471103 OpenBabel07101718192D 39 42 0 0 1 0 0 0 0 0999 V2000 -2.3429 0.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2864 1.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1930 -1.6996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0305 3.0480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 1.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3454 0.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4116 -1.0457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5873 -1.5216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4116 -0.0939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7630 -1.0457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5873 0.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2809 -0.9365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8695 0.7400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4334 -0.2683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3452 1.2004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4953 -2.3470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8547 2.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7630 -0.0939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6260 -1.1385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1610 1.5316 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.3414 1.0654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1236 -0.6723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0305 1.1445 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2902 0.3820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9388 0.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4759 0.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2761 -0.0041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9310 0.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9975 2.0864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -3.2749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6790 3.0480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2274 1.4131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7859 -0.9529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9388 1.3337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7518 0.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4142 -2.0664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8547 1.6204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1145 -0.0939 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 27 1 0 0 0 0 13 35 1 0 0 0 0 14 28 1 1 0 0 0 15 29 2 0 0 0 0 15 35 1 0 0 0 0 16 30 2 0 0 0 0 16 36 1 0 0 0 0 17 31 2 0 0 0 0 17 37 1 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 36 1 1 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 32 2 0 0 0 0 22 27 1 1 0 0 0 22 33 1 0 0 0 0 23 28 1 6 0 0 0 23 37 1 0 0 0 0 24 27 1 1 0 0 0 24 38 1 0 0 0 0 25 34 2 0 0 0 0 25 38 1 0 0 0 0 26 39 1 0 0 0 0 27 28 1 6 0 0 0 28 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.21
Volume:	534.219
LogP:	2.823
LogD:	1.148
LogS:	-3.556
# Rotatable Bonds:	10
TPSA:	151.73
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	5.901
Fsp3:	0.607
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:	-5.402
MDCK Permeability:	8.662143955007195e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.33
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.537
Plasma Protein Binding (PPB):	44.91278076171875%
Volume Distribution (VD):	1.512
Pgp-substrate:	33.26121139526367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.144
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	3.452
Half-life (T1/2):	0.535

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.27
Carcinogencity:	0.166
Eye Corrosion:	0.005
Eye Irritation:	0.05
Respiratory Toxicity:	0.194

Download Data

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

Natural Product: NPC471103

Natural Product ID:	NPC471103
*Common Name:**	ZIVIDPAKHDFBIX-PVFLPAJZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZIVIDPAKHDFBIX-PVFLPAJZSA-N
Standard InCHI:	InChI=1S/C28H34O11/c1-14-12-19(36-16(3)30)22(33)27(13-35-15(2)29)24(38-25(34)18-10-8-7-9-11-18)21(32)20-23(37-17(4)31)28(14,27)39-26(20,5)6/h7-11,14,19-20,22-24,33H,12-13H2,1-6H3/t14-,19+,20?,22+,23-,24-,27+,28-/m1/s1
SMILES:	CC(=O)OC[C@]12[C@@H](O)[C@@H](OC(=O)C)C[C@H]([C@@]32OC(C(C(=O)[C@H]1OC(=O)c1ccccc1)[C@H]3OC(=O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2373439
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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	=	18391.0	nM	PMID[475033]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	18390.0	nM	PMID[475034]
NPT35	Others	n.a.		LogP	=	5.0	n.a.	PMID[475034]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	18197.01	nM	PMID[475034]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Imax	=	91.7	%	PMID[475034]

☑ 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 NPC471103 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	316
0.1-0.2	1059
0.2-0.3	2447
0.3-0.4	4392
0.4-0.5	8795
0.5-0.6	11124
0.6-0.7	11318
0.7-0.8	2659
0.8-0.85	274
0.85-0.9	158
0.9-0.95	145
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC51602
0.9724	High Similarity	NPC106895
0.9655	High Similarity	NPC473670
0.9655	High Similarity	NPC282239
0.9655	High Similarity	NPC21410
0.9645	High Similarity	NPC127857
0.9645	High Similarity	NPC471107
0.9645	High Similarity	NPC471100
0.958	High Similarity	NPC60509
0.958	High Similarity	NPC81698
0.958	High Similarity	NPC250046
0.9524	High Similarity	NPC472393
0.9514	High Similarity	NPC165260
0.9514	High Similarity	NPC161239
0.9514	High Similarity	NPC7095
0.9514	High Similarity	NPC198455
0.9459	High Similarity	NPC471102
0.9456	High Similarity	NPC217091
0.9452	High Similarity	NPC219419
0.9448	High Similarity	NPC306799
0.9448	High Similarity	NPC101043
0.9433	High Similarity	NPC182869
0.9388	High Similarity	NPC228204
0.9388	High Similarity	NPC472549
0.9388	High Similarity	NPC26033
0.9388	High Similarity	NPC114357
0.9388	High Similarity	NPC155329
0.9388	High Similarity	NPC259144
0.9379	High Similarity	NPC473214
0.9379	High Similarity	NPC470245
0.9379	High Similarity	NPC254558
0.9379	High Similarity	NPC112216
0.9362	High Similarity	NPC291599
0.9362	High Similarity	NPC118080
0.9362	High Similarity	NPC27377
0.9362	High Similarity	NPC87448
0.9362	High Similarity	NPC41481
0.9362	High Similarity	NPC97947
0.9362	High Similarity	NPC472576
0.932	High Similarity	NPC158333
0.932	High Similarity	NPC472022
0.932	High Similarity	NPC265395
0.932	High Similarity	NPC134685
0.932	High Similarity	NPC242262
0.932	High Similarity	NPC1173
0.932	High Similarity	NPC256142
0.932	High Similarity	NPC237549
0.932	High Similarity	NPC248265
0.932	High Similarity	NPC473414
0.932	High Similarity	NPC257213
0.932	High Similarity	NPC229545
0.932	High Similarity	NPC472030
0.932	High Similarity	NPC472005
0.932	High Similarity	NPC249471
0.932	High Similarity	NPC11588
0.932	High Similarity	NPC304876
0.9315	High Similarity	NPC470153
0.931	High Similarity	NPC473215
0.931	High Similarity	NPC476975
0.9291	High Similarity	NPC171207
0.9291	High Similarity	NPC97667
0.9291	High Similarity	NPC100913
0.9291	High Similarity	NPC90614
0.9291	High Similarity	NPC275592
0.9257	High Similarity	NPC112523
0.9257	High Similarity	NPC114410
0.9252	High Similarity	NPC477905
0.9252	High Similarity	NPC472548
0.9247	High Similarity	NPC91730
0.9236	High Similarity	NPC301946
0.9236	High Similarity	NPC277053
0.9225	High Similarity	NPC16912
0.9189	High Similarity	NPC77719
0.9184	High Similarity	NPC197037
0.9172	High Similarity	NPC477737
0.9167	High Similarity	NPC470152
0.9167	High Similarity	NPC241951
0.9167	High Similarity	NPC475759
0.9167	High Similarity	NPC471912
0.9167	High Similarity	NPC80895
0.9133	High Similarity	NPC469771
0.9128	High Similarity	NPC132599
0.9128	High Similarity	NPC469730
0.9128	High Similarity	NPC473632
0.911	High Similarity	NPC217918
0.9103	High Similarity	NPC473088
0.9103	High Similarity	NPC70403
0.9103	High Similarity	NPC184817
0.9103	High Similarity	NPC96903
0.9103	High Similarity	NPC171525
0.9103	High Similarity	NPC472575
0.9103	High Similarity	NPC472568
0.9103	High Similarity	NPC469349
0.9103	High Similarity	NPC470157
0.9103	High Similarity	NPC200471
0.9103	High Similarity	NPC470159
0.9103	High Similarity	NPC472571
0.9103	High Similarity	NPC471104
0.9103	High Similarity	NPC158663
0.9103	High Similarity	NPC174982
0.9103	High Similarity	NPC472572
0.9103	High Similarity	NPC29704
0.9103	High Similarity	NPC476973
0.9103	High Similarity	NPC177940
0.9097	High Similarity	NPC477894
0.9097	High Similarity	NPC163087
0.9073	High Similarity	NPC469399
0.9067	High Similarity	NPC11410
0.906	High Similarity	NPC469477
0.906	High Similarity	NPC133430
0.9034	High Similarity	NPC188865
0.9034	High Similarity	NPC95810
0.9034	High Similarity	NPC472570
0.9034	High Similarity	NPC125106
0.9034	High Similarity	NPC475122
0.9034	High Similarity	NPC57628
0.9034	High Similarity	NPC11685
0.9034	High Similarity	NPC163719
0.9034	High Similarity	NPC476974
0.9034	High Similarity	NPC25768
0.9034	High Similarity	NPC472569
0.9034	High Similarity	NPC95265
0.9034	High Similarity	NPC470231
0.9034	High Similarity	NPC70716
0.9034	High Similarity	NPC472573
0.9028	High Similarity	NPC472546
0.9021	High Similarity	NPC472547
0.9007	High Similarity	NPC291638
0.9007	High Similarity	NPC17877
0.9007	High Similarity	NPC472577
0.9007	High Similarity	NPC195647
0.9007	High Similarity	NPC469417
0.9007	High Similarity	NPC66761
0.9	High Similarity	NPC473611
0.9	High Similarity	NPC251139
0.8974	High Similarity	NPC102465
0.8961	High Similarity	NPC66193
0.8936	High Similarity	NPC474608
0.8919	High Similarity	NPC270590
0.8919	High Similarity	NPC471101
0.8919	High Similarity	NPC301556
0.8919	High Similarity	NPC92293
0.8919	High Similarity	NPC266265
0.8912	High Similarity	NPC474935
0.8903	High Similarity	NPC471493
0.8903	High Similarity	NPC471134
0.8897	High Similarity	NPC34012
0.8896	High Similarity	NPC477190
0.8896	High Similarity	NPC43304
0.8896	High Similarity	NPC477188
0.8896	High Similarity	NPC55744
0.8889	High Similarity	NPC477904
0.8889	High Similarity	NPC183270
0.8881	High Similarity	NPC39549
0.8873	High Similarity	NPC477893
0.8873	High Similarity	NPC477896
0.8867	High Similarity	NPC138641
0.8867	High Similarity	NPC22571
0.8867	High Similarity	NPC469648
0.8867	High Similarity	NPC283875
0.8867	High Similarity	NPC469647
0.8851	High Similarity	NPC132652
0.8851	High Similarity	NPC281717
0.8846	High Similarity	NPC61891
0.8844	High Similarity	NPC472556
0.8839	High Similarity	NPC329960
0.8839	High Similarity	NPC150893
0.8839	High Similarity	NPC295408
0.8816	High Similarity	NPC70344
0.8811	High Similarity	NPC472545
0.8811	High Similarity	NPC472551
0.8797	High Similarity	NPC477471
0.8797	High Similarity	NPC477473
0.8797	High Similarity	NPC477466
0.8797	High Similarity	NPC477469
0.8784	High Similarity	NPC469513
0.8776	High Similarity	NPC38696
0.8759	High Similarity	NPC473060
0.8759	High Similarity	NPC48017
0.8759	High Similarity	NPC4341
0.8759	High Similarity	NPC211137
0.8759	High Similarity	NPC184747
0.8759	High Similarity	NPC473613
0.8759	High Similarity	NPC476094
0.8759	High Similarity	NPC43241
0.8759	High Similarity	NPC473758
0.8759	High Similarity	NPC147880
0.8759	High Similarity	NPC473109
0.8759	High Similarity	NPC473085
0.8759	High Similarity	NPC200592
0.8759	High Similarity	NPC473081
0.8759	High Similarity	NPC473112
0.8758	High Similarity	NPC181924
0.8758	High Similarity	NPC477735
0.875	High Similarity	NPC183122
0.875	High Similarity	NPC5115
0.875	High Similarity	NPC283375
0.8742	High Similarity	NPC145649
0.8742	High Similarity	NPC233581
0.8734	High Similarity	NPC40138

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 NPC471103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	717
0.2-0.3	1515
0.3-0.4	2856
0.4-0.5	2285
0.5-0.6	1013
0.6-0.7	451
0.7-0.8	48
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD8407	Phase 2
0.8467	Intermediate Similarity	NPD7236	Approved
0.8415	Intermediate Similarity	NPD8368	Discontinued
0.8395	Intermediate Similarity	NPD7799	Discontinued
0.8312	Intermediate Similarity	NPD7239	Suspended
0.8274	Intermediate Similarity	NPD8434	Phase 2
0.8176	Intermediate Similarity	NPD8435	Approved
0.807	Intermediate Similarity	NPD8361	Approved
0.807	Intermediate Similarity	NPD8360	Approved
0.7973	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD8485	Approved
0.7849	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7057	Phase 3
0.784	Intermediate Similarity	NPD7058	Phase 2
0.7798	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD8150	Discontinued
0.7692	Intermediate Similarity	NPD6190	Approved
0.7688	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7075	Discontinued
0.7531	Intermediate Similarity	NPD6599	Discontinued
0.7465	Intermediate Similarity	NPD4198	Discontinued
0.7439	Intermediate Similarity	NPD6801	Discontinued
0.7434	Intermediate Similarity	NPD7961	Discontinued
0.7407	Intermediate Similarity	NPD8462	Phase 1
0.7405	Intermediate Similarity	NPD4628	Phase 3
0.7394	Intermediate Similarity	NPD2629	Approved
0.7368	Intermediate Similarity	NPD7473	Discontinued
0.7349	Intermediate Similarity	NPD3817	Phase 2
0.7349	Intermediate Similarity	NPD5402	Approved
0.7321	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5761	Phase 2
0.7289	Intermediate Similarity	NPD7819	Suspended
0.7289	Intermediate Similarity	NPD5760	Phase 2
0.7267	Intermediate Similarity	NPD6799	Approved
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7257	Intermediate Similarity	NPD6765	Approved
0.7257	Intermediate Similarity	NPD6764	Approved
0.7219	Intermediate Similarity	NPD8320	Phase 1
0.7219	Intermediate Similarity	NPD8319	Approved
0.7219	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4380	Phase 2
0.7202	Intermediate Similarity	NPD3882	Suspended
0.7198	Intermediate Similarity	NPD6535	Approved
0.7198	Intermediate Similarity	NPD6534	Approved
0.7193	Intermediate Similarity	NPD6232	Discontinued
0.7184	Intermediate Similarity	NPD5844	Phase 1
0.7176	Intermediate Similarity	NPD5494	Approved
0.7174	Intermediate Similarity	NPD7700	Phase 2
0.7174	Intermediate Similarity	NPD7699	Phase 2
0.7165	Intermediate Similarity	NPD8404	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7134	Intermediate Similarity	NPD5403	Approved
0.7126	Intermediate Similarity	NPD37	Approved
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7126	Intermediate Similarity	NPD3818	Discontinued
0.7119	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5401	Approved
0.7117	Intermediate Similarity	NPD2532	Approved
0.7117	Intermediate Similarity	NPD2534	Approved
0.7117	Intermediate Similarity	NPD2533	Approved
0.7113	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6166	Phase 2
0.711	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4966	Approved
0.7101	Intermediate Similarity	NPD4965	Approved
0.7101	Intermediate Similarity	NPD4967	Phase 2
0.7101	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6784	Approved
0.7095	Intermediate Similarity	NPD6785	Approved
0.7095	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8166	Discontinued
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7078	Intermediate Similarity	NPD7008	Discontinued
0.7075	Intermediate Similarity	NPD7741	Discontinued
0.7072	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7048	Intermediate Similarity	NPD3226	Approved
0.7034	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7874	Approved
0.7018	Intermediate Similarity	NPD6234	Discontinued
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6777	Approved
0.7005	Intermediate Similarity	NPD6779	Approved
0.7005	Intermediate Similarity	NPD6776	Approved
0.7005	Intermediate Similarity	NPD6781	Approved
0.7005	Intermediate Similarity	NPD6782	Approved
0.7005	Intermediate Similarity	NPD6780	Approved
0.7005	Intermediate Similarity	NPD6778	Approved
0.6982	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5125	Phase 3
0.698	Remote Similarity	NPD5126	Approved
0.697	Remote Similarity	NPD6273	Approved
0.6966	Remote Similarity	NPD6559	Discontinued
0.6966	Remote Similarity	NPD7251	Discontinued
0.6964	Remote Similarity	NPD7411	Suspended
0.6959	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7228	Approved
0.6928	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7808	Phase 3
0.6923	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD5951	Approved
0.6914	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6797	Phase 2
0.6909	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD230	Phase 1
0.6899	Remote Similarity	NPD6355	Discontinued
0.6895	Remote Similarity	NPD7696	Phase 3
0.6895	Remote Similarity	NPD7698	Approved
0.6895	Remote Similarity	NPD7697	Approved
0.6895	Remote Similarity	NPD7497	Discontinued
0.6894	Remote Similarity	NPD2346	Discontinued
0.6882	Remote Similarity	NPD2801	Approved
0.6872	Remote Similarity	NPD7685	Pre-registration
0.686	Remote Similarity	NPD3749	Approved
0.6859	Remote Similarity	NPD7870	Phase 2
0.6859	Remote Similarity	NPD7871	Phase 2
0.6854	Remote Similarity	NPD7074	Phase 3
0.6853	Remote Similarity	NPD2182	Approved
0.6845	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7701	Phase 2
0.6839	Remote Similarity	NPD7199	Phase 2
0.6829	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD919	Approved
0.6821	Remote Similarity	NPD7801	Approved
0.6807	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2067	Discontinued
0.6798	Remote Similarity	NPD7054	Approved
0.679	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5763	Approved
0.679	Remote Similarity	NPD1471	Phase 3
0.679	Remote Similarity	NPD5762	Approved
0.6778	Remote Similarity	NPD7240	Approved
0.6772	Remote Similarity	NPD6233	Phase 2
0.677	Remote Similarity	NPD2799	Discontinued
0.677	Remote Similarity	NPD7305	Phase 1
0.6768	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7472	Approved
0.6759	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7095	Approved
0.6748	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6959	Discontinued
0.6743	Remote Similarity	NPD1247	Approved
0.6736	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6010	Discontinued
0.6733	Remote Similarity	NPD6319	Approved
0.6728	Remote Similarity	NPD2796	Approved
0.6728	Remote Similarity	NPD2935	Discontinued
0.6723	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6798	Discontinued
0.6709	Remote Similarity	NPD2313	Discontinued
0.6707	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2800	Approved
0.6705	Remote Similarity	NPD7768	Phase 2
0.6687	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3300	Phase 2
0.6684	Remote Similarity	NPD6212	Phase 3
0.6684	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6213	Phase 3
0.6683	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6287	Discontinued
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2575	Approved
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD7610	Discontinued
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD1512	Approved
0.6649	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1549	Phase 2
0.6645	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5048	Discontinued
0.6633	Remote Similarity	NPD8151	Discontinued
0.6627	Remote Similarity	NPD920	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