NPASS Compound

Structure

NPC184550 OpenBabel07101718182D 43 44 0 0 1 0 0 0 0 0999 V2000 1.4538 11.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5160 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 10.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 9.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 8.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 8.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 7.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 6.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 5.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7839 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -0.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0519 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0519 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1859 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3198 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0519 -2.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6736 0.1280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2782 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 2.3090 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 1.4538 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 23 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 19 1 0 0 0 0 17 38 1 0 0 0 0 18 39 1 0 0 0 0 20 33 2 0 0 0 0 20 39 1 0 0 0 0 21 15 1 1 0 0 0 21 24 1 0 0 0 0 21 40 1 0 0 0 0 22 16 1 6 0 0 0 22 25 1 0 0 0 0 22 42 1 0 0 0 0 23 34 2 0 0 0 0 23 41 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 6 0 0 0 25 28 1 0 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 38 1 1 0 0 0 27 29 1 0 0 0 0 27 41 1 6 0 0 0 28 30 1 6 0 0 0 28 37 1 0 0 0 0 29 40 1 0 0 0 0 29 43 1 6 0 0 0 30 18 1 1 0 0 0 30 42 1 0 0 0 0 30 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.36
Volume:	619.323
LogP:	3.552
LogD:	2.755
LogS:	-3.705
# Rotatable Bonds:	22
TPSA:	190.67
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.097
Synthetic Accessibility Score:	4.726
Fsp3:	0.933
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.372
MDCK Permeability:	5.39688189746812e-05
Pgp-inhibitor:	0.891
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	91.74211883544922%
Volume Distribution (VD):	0.691
Pgp-substrate:	4.622566223144531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	2.821
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.564
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.174
AMES Toxicity:	0.285
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.633
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC184550

Natural Product ID:	NPC184550
*Common Name:**	Physordinose C
IUPAC Name:	[(2R,3R,4S,5R,6R)-2-[(2S,3S,4S,5R)-2-(acetyloxymethyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(2-methylpropoxy)oxan-3-yl] dodecanoate
Synonyms:	Physordinose C
Standard InCHIKey:	WCUYNFHBYFOUKI-UTGHZIEOSA-N
Standard InCHI:	InChI=1S/C30H54O13/c1-5-6-7-8-9-10-11-12-13-14-23(34)41-27-26(38-17-19(2)3)24(35)21(15-31)40-29(27)43-30(18-39-20(4)33)28(37)25(36)22(16-32)42-30/h19,21-22,24-29,31-32,35-37H,5-18H2,1-4H3/t21-,22-,24-,25-,26+,27-,28+,29-,30+/m1/s1
SMILES:	CCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@@H]1O[C@@]1(COC(=O)C)[C@H]([C@@H]([C@@H](CO)O1)O)O)O)OCC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171817
PubChem CID:	46872116
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO23525	Physalis sordida	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20575572]
NPO23525	Physalis sordida	Species	Solanaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	340.0	nM	PMID[457237]

☑ 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 NPC184550 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	506
0.1-0.2	4197
0.2-0.3	12876
0.3-0.4	11146
0.4-0.5	7944
0.5-0.6	5065
0.6-0.7	786
0.7-0.8	159
0.8-0.85	9
0.85-0.9	4
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC185419
0.9851	High Similarity	NPC308096
0.9851	High Similarity	NPC291228
0.9394	High Similarity	NPC206601
0.9118	High Similarity	NPC285003
0.9118	High Similarity	NPC241265
0.8971	High Similarity	NPC97736
0.8971	High Similarity	NPC50228
0.8841	High Similarity	NPC211428
0.8788	High Similarity	NPC325773
0.8732	High Similarity	NPC163812
0.8732	High Similarity	NPC206823
0.8533	High Similarity	NPC477346
0.8533	High Similarity	NPC158302
0.8533	High Similarity	NPC294748
0.8533	High Similarity	NPC22742
0.8533	High Similarity	NPC146992
0.8533	High Similarity	NPC85759
0.8533	High Similarity	NPC477344
0.8529	High Similarity	NPC12040
0.8529	High Similarity	NPC76881
0.8472	Intermediate Similarity	NPC39266
0.8472	Intermediate Similarity	NPC169085
0.8472	Intermediate Similarity	NPC225748
0.8472	Intermediate Similarity	NPC9763
0.8421	Intermediate Similarity	NPC267592
0.8378	Intermediate Similarity	NPC477350
0.8312	Intermediate Similarity	NPC238056
0.8312	Intermediate Similarity	NPC269318
0.8312	Intermediate Similarity	NPC307400
0.8312	Intermediate Similarity	NPC290012
0.8312	Intermediate Similarity	NPC475667
0.8312	Intermediate Similarity	NPC27289
0.8312	Intermediate Similarity	NPC472204
0.8312	Intermediate Similarity	NPC183888
0.8312	Intermediate Similarity	NPC184915
0.8312	Intermediate Similarity	NPC472202
0.8312	Intermediate Similarity	NPC224953
0.8312	Intermediate Similarity	NPC477331
0.8312	Intermediate Similarity	NPC472201
0.8312	Intermediate Similarity	NPC475327
0.8312	Intermediate Similarity	NPC119583
0.8312	Intermediate Similarity	NPC476087
0.8312	Intermediate Similarity	NPC143421
0.8312	Intermediate Similarity	NPC123204
0.8312	Intermediate Similarity	NPC297768
0.8312	Intermediate Similarity	NPC173328
0.8312	Intermediate Similarity	NPC477318
0.8312	Intermediate Similarity	NPC44782
0.8312	Intermediate Similarity	NPC169345
0.8312	Intermediate Similarity	NPC186992
0.8312	Intermediate Similarity	NPC89843
0.8312	Intermediate Similarity	NPC259294
0.8312	Intermediate Similarity	NPC477317
0.8312	Intermediate Similarity	NPC115013
0.8312	Intermediate Similarity	NPC126685
0.8312	Intermediate Similarity	NPC472203
0.8312	Intermediate Similarity	NPC472200
0.8312	Intermediate Similarity	NPC475270
0.8312	Intermediate Similarity	NPC477319
0.8312	Intermediate Similarity	NPC472205
0.8312	Intermediate Similarity	NPC477347
0.8267	Intermediate Similarity	NPC476781
0.8267	Intermediate Similarity	NPC476782
0.8267	Intermediate Similarity	NPC216883
0.8267	Intermediate Similarity	NPC476783
0.8261	Intermediate Similarity	NPC471761
0.8261	Intermediate Similarity	NPC471760
0.8261	Intermediate Similarity	NPC190418
0.8228	Intermediate Similarity	NPC288471
0.8169	Intermediate Similarity	NPC250619
0.8158	Intermediate Similarity	NPC113745
0.8158	Intermediate Similarity	NPC477323
0.8158	Intermediate Similarity	NPC477329
0.8158	Intermediate Similarity	NPC146380
0.8158	Intermediate Similarity	NPC109887
0.8158	Intermediate Similarity	NPC477325
0.8158	Intermediate Similarity	NPC475425
0.8158	Intermediate Similarity	NPC477328
0.8158	Intermediate Similarity	NPC281563
0.8158	Intermediate Similarity	NPC477330
0.8158	Intermediate Similarity	NPC477320
0.8158	Intermediate Similarity	NPC477326
0.8101	Intermediate Similarity	NPC60849
0.8101	Intermediate Similarity	NPC477332
0.8101	Intermediate Similarity	NPC472352
0.8049	Intermediate Similarity	NPC470009
0.7971	Intermediate Similarity	NPC268243
0.7941	Intermediate Similarity	NPC472026
0.7917	Intermediate Similarity	NPC67099
0.7879	Intermediate Similarity	NPC148424
0.7848	Intermediate Similarity	NPC236649
0.7848	Intermediate Similarity	NPC21693
0.7805	Intermediate Similarity	NPC470657
0.7711	Intermediate Similarity	NPC314364
0.7711	Intermediate Similarity	NPC51662
0.7711	Intermediate Similarity	NPC31349
0.7703	Intermediate Similarity	NPC53760
0.7703	Intermediate Similarity	NPC52268
0.7681	Intermediate Similarity	NPC477757
0.7681	Intermediate Similarity	NPC477763
0.7681	Intermediate Similarity	NPC477753
0.7681	Intermediate Similarity	NPC477750
0.7681	Intermediate Similarity	NPC477762
0.7681	Intermediate Similarity	NPC477755
0.7654	Intermediate Similarity	NPC473500
0.7654	Intermediate Similarity	NPC38295
0.7654	Intermediate Similarity	NPC156089
0.7654	Intermediate Similarity	NPC470313
0.7647	Intermediate Similarity	NPC320032
0.7647	Intermediate Similarity	NPC322855
0.7639	Intermediate Similarity	NPC477764
0.7639	Intermediate Similarity	NPC477756
0.7639	Intermediate Similarity	NPC477752
0.7639	Intermediate Similarity	NPC477751
0.7576	Intermediate Similarity	NPC23155
0.7576	Intermediate Similarity	NPC469937
0.7576	Intermediate Similarity	NPC53463
0.7576	Intermediate Similarity	NPC320588
0.7561	Intermediate Similarity	NPC473791
0.7536	Intermediate Similarity	NPC470363
0.7534	Intermediate Similarity	NPC477759
0.7534	Intermediate Similarity	NPC477758
0.7534	Intermediate Similarity	NPC32148
0.7534	Intermediate Similarity	NPC477754
0.7534	Intermediate Similarity	NPC477761
0.7534	Intermediate Similarity	NPC477760
0.75	Intermediate Similarity	NPC219040
0.75	Intermediate Similarity	NPC472025
0.747	Intermediate Similarity	NPC83839
0.7439	Intermediate Similarity	NPC474266
0.7424	Intermediate Similarity	NPC323361
0.7424	Intermediate Similarity	NPC130683
0.7391	Intermediate Similarity	NPC34877
0.7391	Intermediate Similarity	NPC290179
0.7342	Intermediate Similarity	NPC110813
0.7342	Intermediate Similarity	NPC474003
0.7342	Intermediate Similarity	NPC70996
0.7333	Intermediate Similarity	NPC58267
0.7333	Intermediate Similarity	NPC263674
0.7333	Intermediate Similarity	NPC261372
0.7317	Intermediate Similarity	NPC475849
0.7308	Intermediate Similarity	NPC228411
0.7303	Intermediate Similarity	NPC215570
0.7297	Intermediate Similarity	NPC469925
0.725	Intermediate Similarity	NPC133377
0.725	Intermediate Similarity	NPC475616
0.7237	Intermediate Similarity	NPC321873
0.7222	Intermediate Similarity	NPC474297
0.7222	Intermediate Similarity	NPC54731
0.72	Intermediate Similarity	NPC82315
0.7195	Intermediate Similarity	NPC216941
0.7191	Intermediate Similarity	NPC477348
0.7191	Intermediate Similarity	NPC238264
0.7191	Intermediate Similarity	NPC477345
0.7159	Intermediate Similarity	NPC477349
0.7159	Intermediate Similarity	NPC472197
0.7143	Intermediate Similarity	NPC253975
0.7143	Intermediate Similarity	NPC472273
0.7143	Intermediate Similarity	NPC476613
0.7143	Intermediate Similarity	NPC236580
0.7143	Intermediate Similarity	NPC304445
0.7143	Intermediate Similarity	NPC125253
0.7143	Intermediate Similarity	NPC192025
0.7143	Intermediate Similarity	NPC476612
0.7121	Intermediate Similarity	NPC233726
0.7121	Intermediate Similarity	NPC23134
0.7121	Intermediate Similarity	NPC124963
0.7121	Intermediate Similarity	NPC326533
0.7105	Intermediate Similarity	NPC28526
0.7079	Intermediate Similarity	NPC320089
0.7067	Intermediate Similarity	NPC286842
0.7059	Intermediate Similarity	NPC303727
0.7059	Intermediate Similarity	NPC478111
0.7051	Intermediate Similarity	NPC51249
0.7051	Intermediate Similarity	NPC474100
0.7051	Intermediate Similarity	NPC473775
0.7051	Intermediate Similarity	NPC475260
0.7051	Intermediate Similarity	NPC473699
0.7051	Intermediate Similarity	NPC475232
0.7033	Intermediate Similarity	NPC475164
0.7033	Intermediate Similarity	NPC475785
0.7033	Intermediate Similarity	NPC475765
0.7033	Intermediate Similarity	NPC475593
0.7033	Intermediate Similarity	NPC473605
0.7033	Intermediate Similarity	NPC306041
0.7033	Intermediate Similarity	NPC476066
0.7033	Intermediate Similarity	NPC475525
0.7033	Intermediate Similarity	NPC475540
0.7033	Intermediate Similarity	NPC473765
0.7033	Intermediate Similarity	NPC475375
0.7033	Intermediate Similarity	NPC475241
0.7	Intermediate Similarity	NPC44682
0.7	Intermediate Similarity	NPC163409
0.6989	Remote Similarity	NPC473146
0.6977	Remote Similarity	NPC471411
0.6977	Remote Similarity	NPC471410
0.697	Remote Similarity	NPC323574
0.6966	Remote Similarity	NPC472199
0.6966	Remote Similarity	NPC235051

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 NPC184550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	655
0.1-0.2	4057
0.2-0.3	2908
0.3-0.4	803
0.4-0.5	480
0.5-0.6	194
0.6-0.7	45
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7576	Intermediate Similarity	NPD3730	Approved
0.7576	Intermediate Similarity	NPD3728	Approved
0.7534	Intermediate Similarity	NPD897	Approved
0.7534	Intermediate Similarity	NPD898	Approved
0.7534	Intermediate Similarity	NPD896	Approved
0.7424	Intermediate Similarity	NPD887	Approved
0.7424	Intermediate Similarity	NPD889	Approved
0.7424	Intermediate Similarity	NPD894	Approved
0.7424	Intermediate Similarity	NPD895	Approved
0.7353	Intermediate Similarity	NPD2267	Suspended
0.7273	Intermediate Similarity	NPD2269	Approved
0.716	Intermediate Similarity	NPD7329	Approved
0.7121	Intermediate Similarity	NPD904	Phase 3
0.7121	Intermediate Similarity	NPD905	Approved
0.7051	Intermediate Similarity	NPD3181	Approved
0.7013	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD888	Phase 3
0.6912	Remote Similarity	NPD893	Approved
0.6912	Remote Similarity	NPD892	Phase 3
0.6912	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD891	Phase 3
0.6757	Remote Similarity	NPD8961	Approved
0.6712	Remote Similarity	NPD6123	Approved
0.6667	Remote Similarity	NPD8138	Approved
0.6667	Remote Similarity	NPD8085	Approved
0.6667	Remote Similarity	NPD8082	Approved
0.6667	Remote Similarity	NPD7909	Approved
0.6667	Remote Similarity	NPD8083	Approved
0.6667	Remote Similarity	NPD8084	Approved
0.6667	Remote Similarity	NPD8086	Approved
0.6667	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8139	Approved
0.6598	Remote Similarity	NPD8276	Approved
0.6598	Remote Similarity	NPD8275	Approved
0.6533	Remote Similarity	NPD847	Phase 1
0.6531	Remote Similarity	NPD8081	Approved
0.6531	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6686	Approved
0.6484	Remote Similarity	NPD46	Approved
0.6484	Remote Similarity	NPD6698	Approved
0.6465	Remote Similarity	NPD8393	Approved
0.6437	Remote Similarity	NPD3669	Approved
0.6437	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4238	Approved
0.6429	Remote Similarity	NPD4802	Phase 2
0.64	Remote Similarity	NPD8140	Approved
0.64	Remote Similarity	NPD8307	Discontinued
0.6364	Remote Similarity	NPD8998	Phase 2
0.6364	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9000	Phase 3
0.6364	Remote Similarity	NPD8997	Approved
0.6364	Remote Similarity	NPD8993	Phase 1
0.6364	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8999	Phase 3
0.6338	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7346	Approved
0.6301	Remote Similarity	NPD8959	Approved
0.6275	Remote Similarity	NPD8306	Approved
0.6275	Remote Similarity	NPD8305	Approved
0.6275	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8087	Discontinued
0.6212	Remote Similarity	NPD2699	Approved
0.6207	Remote Similarity	NPD1780	Approved
0.6207	Remote Similarity	NPD1779	Approved
0.619	Remote Similarity	NPD8133	Approved
0.6176	Remote Similarity	NPD8966	Approved
0.6176	Remote Similarity	NPD8965	Approved
0.6164	Remote Similarity	NPD73	Approved
0.6154	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD3198	Approved
0.6087	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6412	Phase 2
0.6064	Remote Similarity	NPD7983	Approved
0.6061	Remote Similarity	NPD9006	Approved
0.6026	Remote Similarity	NPD1457	Discontinued
0.6019	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8171	Discontinued
0.5972	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD9036	Phase 3
0.5962	Remote Similarity	NPD6941	Approved
0.5955	Remote Similarity	NPD883	Phase 2
0.5955	Remote Similarity	NPD882	Phase 2
0.5946	Remote Similarity	NPD8513	Phase 3
0.5946	Remote Similarity	NPD8516	Approved
0.5946	Remote Similarity	NPD8517	Approved
0.5946	Remote Similarity	NPD8515	Approved
0.5926	Remote Similarity	NPD6940	Discontinued
0.5915	Remote Similarity	NPD1400	Approved
0.5915	Remote Similarity	NPD1399	Approved
0.5909	Remote Similarity	NPD8788	Approved
0.5882	Remote Similarity	NPD2257	Approved
0.5872	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD369	Approved
0.5851	Remote Similarity	NPD3716	Discontinued
0.5842	Remote Similarity	NPD8300	Approved
0.5842	Remote Similarity	NPD8301	Approved
0.5833	Remote Similarity	NPD1447	Phase 3
0.5833	Remote Similarity	NPD1446	Phase 3
0.5818	Remote Similarity	NPD7641	Discontinued
0.5816	Remote Similarity	NPD6428	Approved
0.5811	Remote Similarity	NPD884	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD885	Approved
0.5804	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD1811	Approved
0.5765	Remote Similarity	NPD1810	Approved
0.5758	Remote Similarity	NPD2270	Approved
0.5752	Remote Similarity	NPD8080	Discontinued
0.5714	Remote Similarity	NPD8347	Approved
0.5714	Remote Similarity	NPD8345	Approved
0.5714	Remote Similarity	NPD8346	Approved
0.57	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.57	Remote Similarity	NPD2255	Approved
0.5698	Remote Similarity	NPD11	Approved
0.5698	Remote Similarity	NPD376	Approved
0.5686	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD7139	Approved
0.5686	Remote Similarity	NPD7140	Approved
0.5682	Remote Similarity	NPD6118	Approved
0.5682	Remote Similarity	NPD6115	Approved
0.5682	Remote Similarity	NPD6697	Approved
0.5682	Remote Similarity	NPD6114	Approved
0.5664	Remote Similarity	NPD8444	Approved
0.5663	Remote Similarity	NPD8277	Approved
0.5657	Remote Similarity	NPD7839	Suspended
0.5638	Remote Similarity	NPD4250	Approved
0.5638	Remote Similarity	NPD4251	Approved
0.5625	Remote Similarity	NPD3197	Phase 1
0.5616	Remote Similarity	NPD9010	Approved
0.5616	Remote Similarity	NPD65	Approved
0.5616	Remote Similarity	NPD9050	Approved
0.5616	Remote Similarity	NPD9007	Approved
0.5616	Remote Similarity	NPD9049	Discontinued
0.5616	Remote Similarity	NPD8960	Approved
0.5616	Remote Similarity	NPD66	Approved
0.5616	Remote Similarity	NPD9011	Approved
0.5616	Remote Similarity	NPD9009	Approved
0.5616	Remote Similarity	NPD64	Approved
0.5616	Remote Similarity	NPD9008	Approved
0.5616	Remote Similarity	NPD72	Approved
0.5606	Remote Similarity	NPD7536	Approved
0.5604	Remote Similarity	NPD7345	Approved
0.5604	Remote Similarity	NPD6435	Approved
0.5603	Remote Similarity	NPD7507	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