NPASS Compound

Structure

CID193798 OpenBabel06191715582D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.0186 -3.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0443 -3.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3310 -3.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6177 -3.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -0.5781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3566 -3.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9174 -1.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4771 -1.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1049 -4.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0793 -4.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6177 -4.9674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4302 -2.1460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 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 22 1 0 0 0 0 2 22 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 18 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 32 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 14 2 0 0 0 0 13 32 1 0 0 0 0 14 19 1 0 0 0 0 15 23 1 6 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 6 0 0 0 17 25 1 0 0 0 0 17 27 2 0 0 0 0 18 28 2 0 0 0 0 18 29 1 0 0 0 0 19 24 1 1 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 20 34 1 0 0 0 0 21 30 2 0 0 0 0 21 33 1 0 0 0 0 22 31 1 0 0 0 0 23 3 1 6 0 0 0 24 26 1 1 0 0 0 25 26 1 1 0 0 0 26 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.21
Volume:	469.973
LogP:	2.459
LogD:	0.9
LogS:	-4.001
# Rotatable Bonds:	4
TPSA:	126.57
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	5.65
Fsp3:	0.654
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:	-5.503
MDCK Permeability:	1.429994881618768e-05
Pgp-inhibitor:	0.049
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.675
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.525
Plasma Protein Binding (PPB):	74.88923645019531%
Volume Distribution (VD):	0.399
Pgp-substrate:	19.062421798706055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.264
CYP2C9-inhibitor:	0.254
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	5.619
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.839
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.766
Skin Sensitization:	0.182
Carcinogencity:	0.429
Eye Corrosion:	0.046
Eye Irritation:	0.302
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC193798

Natural Product ID:	NPC193798
*Common Name:**	GUIYORVNNIUEBH-SXMAHZFBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GUIYORVNNIUEBH-SXMAHZFBSA-N
Standard InCHI:	InChI=1S/C26H32O8/c1-22(2,31)16-12-17(27)25(5)15(23(16,3)9-7-18(28)29)6-10-24(4)19(14-8-11-32-13-14)33-21(30)20-26(24,25)34-20/h7-9,11,13,15-16,19-20,31H,6,10,12H2,1-5H3,(H,28,29)/b9-7-/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1
SMILES:	CC(C)([C@@H]1CC(=O)[C@]2(C)[C@H](CC[C@@]3(C)[C@H](c4ccoc4)OC(=O)[C@@H]4[C@]23O4)[C@@]1(C)/C=CC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1865426
PubChem CID:	44144270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	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
Potency	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[496314]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[496314]

☑ 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 NPC193798 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	352
0.1-0.2	1424
0.2-0.3	3153
0.3-0.4	5662
0.4-0.5	10495
0.5-0.6	10222
0.6-0.7	9096
0.7-0.8	1882
0.8-0.85	248
0.85-0.9	99
0.9-0.95	52
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC25255
0.974	High Similarity	NPC476856
0.974	High Similarity	NPC123088
0.974	High Similarity	NPC476857
0.974	High Similarity	NPC476858
0.9737	High Similarity	NPC477403
0.9615	High Similarity	NPC476861
0.9615	High Similarity	NPC476850
0.9615	High Similarity	NPC476853
0.9613	High Similarity	NPC476860
0.9608	High Similarity	NPC237155
0.9551	High Similarity	NPC23387
0.9545	High Similarity	NPC472653
0.9545	High Similarity	NPC477402
0.949	High Similarity	NPC472282
0.949	High Similarity	NPC173516
0.9487	High Similarity	NPC470940
0.9484	High Similarity	NPC5079
0.9484	High Similarity	NPC470939
0.9484	High Similarity	NPC329938
0.9477	High Similarity	NPC263265
0.9477	High Similarity	NPC60973
0.943	High Similarity	NPC160651
0.943	High Similarity	NPC471397
0.9423	High Similarity	NPC234660
0.9423	High Similarity	NPC292389
0.9423	High Similarity	NPC39986
0.9423	High Similarity	NPC51568
0.9423	High Similarity	NPC302369
0.9423	High Similarity	NPC469338
0.9423	High Similarity	NPC134254
0.9423	High Similarity	NPC477405
0.9419	High Similarity	NPC335761
0.9419	High Similarity	NPC305016
0.9416	High Similarity	NPC286722
0.9363	High Similarity	NPC276551
0.9363	High Similarity	NPC469849
0.9359	High Similarity	NPC263432
0.9359	High Similarity	NPC82851
0.9359	High Similarity	NPC69028
0.9355	High Similarity	NPC475295
0.9355	High Similarity	NPC473473
0.9351	High Similarity	NPC469485
0.9351	High Similarity	NPC107646
0.9351	High Similarity	NPC126723
0.9351	High Similarity	NPC209364
0.9304	High Similarity	NPC470875
0.9295	High Similarity	NPC475381
0.929	High Similarity	NPC173544
0.929	High Similarity	NPC249021
0.929	High Similarity	NPC472283
0.9286	High Similarity	NPC264943
0.9245	High Similarity	NPC472775
0.9245	High Similarity	NPC472651
0.9245	High Similarity	NPC473753
0.9245	High Similarity	NPC473766
0.9245	High Similarity	NPC472774
0.9236	High Similarity	NPC472771
0.9236	High Similarity	NPC96443
0.9236	High Similarity	NPC117986
0.9236	High Similarity	NPC290400
0.9187	High Similarity	NPC271235
0.9187	High Similarity	NPC472652
0.9177	High Similarity	NPC472773
0.9167	High Similarity	NPC472772
0.9167	High Similarity	NPC45101
0.9161	High Similarity	NPC469336
0.9161	High Similarity	NPC469850
0.9156	High Similarity	NPC75906
0.9097	High Similarity	NPC178932
0.9097	High Similarity	NPC282445
0.9057	High Similarity	NPC476197
0.9057	High Similarity	NPC224394
0.9057	High Similarity	NPC663
0.9057	High Similarity	NPC469846
0.9051	High Similarity	NPC191828
0.9045	High Similarity	NPC299038
0.9045	High Similarity	NPC187149
0.9045	High Similarity	NPC167142
0.9045	High Similarity	NPC36655
0.9045	High Similarity	NPC261597
0.9038	High Similarity	NPC281258
0.9038	High Similarity	NPC214541
0.9038	High Similarity	NPC44675
0.9026	High Similarity	NPC159927
0.9026	High Similarity	NPC469335
0.9026	High Similarity	NPC477404
0.9026	High Similarity	NPC46551
0.9026	High Similarity	NPC196864
0.9013	High Similarity	NPC262198
0.9	High Similarity	NPC271657
0.8994	High Similarity	NPC18347
0.8994	High Similarity	NPC200782
0.8994	High Similarity	NPC149896
0.8987	High Similarity	NPC475967
0.8987	High Similarity	NPC473368
0.897	High Similarity	NPC478177
0.8968	High Similarity	NPC18135
0.8963	High Similarity	NPC471437
0.8957	High Similarity	NPC159232
0.8944	High Similarity	NPC475779
0.891	High Similarity	NPC44577
0.891	High Similarity	NPC476201
0.891	High Similarity	NPC469503
0.8896	High Similarity	NPC470995
0.8882	High Similarity	NPC86935
0.8882	High Similarity	NPC470182
0.8875	High Similarity	NPC197596
0.8875	High Similarity	NPC207978
0.8854	High Similarity	NPC30222
0.8854	High Similarity	NPC57998
0.8831	High Similarity	NPC221809
0.8831	High Similarity	NPC470941
0.8827	High Similarity	NPC149945
0.8827	High Similarity	NPC478178
0.882	High Similarity	NPC288602
0.882	High Similarity	NPC88841
0.882	High Similarity	NPC419
0.8797	High Similarity	NPC35000
0.8797	High Similarity	NPC476262
0.8788	High Similarity	NPC469848
0.8782	High Similarity	NPC476122
0.878	High Similarity	NPC82602
0.878	High Similarity	NPC302392
0.8766	High Similarity	NPC346
0.8758	High Similarity	NPC188649
0.8758	High Similarity	NPC476944
0.875	High Similarity	NPC307383
0.8735	High Similarity	NPC236004
0.8727	High Similarity	NPC169299
0.8727	High Similarity	NPC285227
0.8727	High Similarity	NPC160818
0.8712	High Similarity	NPC121995
0.871	High Similarity	NPC250228
0.871	High Similarity	NPC255414
0.8706	High Similarity	NPC247563
0.8706	High Similarity	NPC105395
0.8706	High Similarity	NPC242068
0.8704	High Similarity	NPC198047
0.8696	High Similarity	NPC470789
0.8696	High Similarity	NPC287559
0.8683	High Similarity	NPC262386
0.8679	High Similarity	NPC75310
0.8671	High Similarity	NPC268905
0.8659	High Similarity	NPC478179
0.8659	High Similarity	NPC270312
0.8659	High Similarity	NPC472764
0.8659	High Similarity	NPC476224
0.865	High Similarity	NPC261184
0.8642	High Similarity	NPC471167
0.8642	High Similarity	NPC6326
0.8642	High Similarity	NPC471166
0.8642	High Similarity	NPC18986
0.8642	High Similarity	NPC68848
0.8642	High Similarity	NPC472767
0.8642	High Similarity	NPC211777
0.8636	High Similarity	NPC142113
0.8636	High Similarity	NPC137295
0.8634	High Similarity	NPC262872
0.8627	High Similarity	NPC121158
0.8625	High Similarity	NPC41880
0.8623	High Similarity	NPC94763
0.8616	High Similarity	NPC114880
0.8609	High Similarity	NPC476943
0.8608	High Similarity	NPC272590
0.8606	High Similarity	NPC296558
0.8606	High Similarity	NPC472765
0.8606	High Similarity	NPC472766
0.8599	High Similarity	NPC69647
0.8599	High Similarity	NPC125182
0.8599	High Similarity	NPC472654
0.8599	High Similarity	NPC195325
0.8598	High Similarity	NPC97574
0.8598	High Similarity	NPC93172
0.8598	High Similarity	NPC214600
0.8598	High Similarity	NPC472141
0.8589	High Similarity	NPC165218
0.8589	High Similarity	NPC472139
0.8589	High Similarity	NPC471168
0.8571	High Similarity	NPC195954
0.8571	High Similarity	NPC267632
0.8571	High Similarity	NPC472776
0.8571	High Similarity	NPC472777
0.8571	High Similarity	NPC243577
0.8571	High Similarity	NPC472778
0.8571	High Similarity	NPC470118
0.8571	High Similarity	NPC88007
0.8562	High Similarity	NPC92979
0.8553	High Similarity	NPC475777
0.8544	High Similarity	NPC156189
0.8537	High Similarity	NPC146991
0.8537	High Similarity	NPC56358
0.8528	High Similarity	NPC472668
0.8521	High Similarity	NPC472665
0.8519	High Similarity	NPC474611
0.8519	High Similarity	NPC475226
0.8516	High Similarity	NPC251865
0.8512	High Similarity	NPC471632
0.8509	High Similarity	NPC204663
0.8494	Intermediate Similarity	NPC327922

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 NPC193798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	1019
0.2-0.3	2133
0.3-0.4	2637
0.4-0.5	1898
0.5-0.6	854
0.6-0.7	270
0.7-0.8	31
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8447	Intermediate Similarity	NPD5760	Phase 2
0.8447	Intermediate Similarity	NPD5761	Phase 2
0.843	Intermediate Similarity	NPD8434	Phase 2
0.8242	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6765	Approved
0.7829	Intermediate Similarity	NPD6764	Approved
0.7751	Intermediate Similarity	NPD7075	Discontinued
0.7679	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6784	Approved
0.7654	Intermediate Similarity	NPD6785	Approved
0.75	Intermediate Similarity	NPD6599	Discontinued
0.7471	Intermediate Similarity	NPD7819	Suspended
0.744	Intermediate Similarity	NPD3226	Approved
0.743	Intermediate Similarity	NPD6559	Discontinued
0.7412	Intermediate Similarity	NPD6801	Discontinued
0.7378	Intermediate Similarity	NPD4628	Phase 3
0.7353	Intermediate Similarity	NPD7411	Suspended
0.7351	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5402	Approved
0.7301	Intermediate Similarity	NPD1471	Phase 3
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6799	Approved
0.7241	Intermediate Similarity	NPD3749	Approved
0.7236	Intermediate Similarity	NPD8404	Phase 2
0.7225	Intermediate Similarity	NPD3817	Phase 2
0.7219	Intermediate Similarity	NPD5403	Approved
0.7216	Intermediate Similarity	NPD1247	Approved
0.7212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD919	Approved
0.7195	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3882	Suspended
0.7169	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5494	Approved
0.7158	Intermediate Similarity	NPD8313	Approved
0.7158	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD7473	Discontinued
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7118	Intermediate Similarity	NPD920	Approved
0.7111	Intermediate Similarity	NPD3751	Discontinued
0.7101	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5401	Approved
0.7095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4380	Phase 2
0.7091	Intermediate Similarity	NPD2346	Discontinued
0.7086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5844	Phase 1
0.7069	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6099	Approved
0.703	Intermediate Similarity	NPD6100	Approved
0.7017	Intermediate Similarity	NPD7799	Discontinued
0.7017	Intermediate Similarity	NPD3818	Discontinued
0.7011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1934	Approved
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3787	Discontinued
0.6983	Remote Similarity	NPD6232	Discontinued
0.6982	Remote Similarity	NPD7236	Approved
0.6974	Remote Similarity	NPD7435	Discontinued
0.6957	Remote Similarity	NPD7251	Discontinued
0.6946	Remote Similarity	NPD1549	Phase 2
0.6943	Remote Similarity	NPD8285	Discontinued
0.6936	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7458	Discontinued
0.6928	Remote Similarity	NPD1551	Phase 2
0.6927	Remote Similarity	NPD8127	Discontinued
0.6927	Remote Similarity	NPD6959	Discontinued
0.6923	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7808	Phase 3
0.6914	Remote Similarity	NPD3268	Approved
0.6902	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6797	Phase 2
0.689	Remote Similarity	NPD6355	Discontinued
0.6886	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7239	Suspended
0.6867	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD2799	Discontinued
0.6865	Remote Similarity	NPD7685	Pre-registration
0.686	Remote Similarity	NPD6273	Approved
0.6851	Remote Similarity	NPD3926	Phase 2
0.6848	Remote Similarity	NPD7074	Phase 3
0.6845	Remote Similarity	NPD8407	Phase 2
0.6829	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD37	Approved
0.681	Remote Similarity	NPD2313	Discontinued
0.6805	Remote Similarity	NPD2800	Approved
0.6802	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4965	Approved
0.6798	Remote Similarity	NPD7768	Phase 2
0.6798	Remote Similarity	NPD4967	Phase 2
0.6798	Remote Similarity	NPD4966	Approved
0.6793	Remote Similarity	NPD7054	Approved
0.679	Remote Similarity	NPD6832	Phase 2
0.6786	Remote Similarity	NPD5762	Approved
0.6786	Remote Similarity	NPD5763	Approved
0.6786	Remote Similarity	NPD2344	Approved
0.678	Remote Similarity	NPD2801	Approved
0.6774	Remote Similarity	NPD8368	Discontinued
0.6766	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7874	Approved
0.6765	Remote Similarity	NPD3750	Approved
0.6763	Remote Similarity	NPD7907	Approved
0.6758	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7472	Approved
0.6746	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6777	Approved
0.6735	Remote Similarity	NPD6778	Approved
0.6735	Remote Similarity	NPD6779	Approved
0.6735	Remote Similarity	NPD6776	Approved
0.6735	Remote Similarity	NPD6780	Approved
0.6735	Remote Similarity	NPD6782	Approved
0.6735	Remote Similarity	NPD6781	Approved
0.6726	Remote Similarity	NPD2935	Discontinued
0.6722	Remote Similarity	NPD6234	Discontinued
0.6717	Remote Similarity	NPD7696	Phase 3
0.6717	Remote Similarity	NPD7698	Approved
0.6717	Remote Similarity	NPD7697	Approved
0.6706	Remote Similarity	NPD1243	Approved
0.6702	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD447	Suspended
0.6685	Remote Similarity	NPD1465	Phase 2
0.6683	Remote Similarity	NPD7871	Phase 2
0.6683	Remote Similarity	NPD8319	Approved
0.6683	Remote Similarity	NPD7870	Phase 2
0.6683	Remote Similarity	NPD8320	Phase 1
0.6667	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1510	Phase 2
0.665	Remote Similarity	NPD4107	Approved
0.6649	Remote Similarity	NPD7228	Approved
0.6646	Remote Similarity	NPD7095	Approved
0.663	Remote Similarity	NPD2403	Approved
0.6629	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2309	Approved
0.6628	Remote Similarity	NPD6190	Approved
0.6628	Remote Similarity	NPD3887	Approved
0.6625	Remote Similarity	NPD1608	Approved
0.6612	Remote Similarity	NPD6808	Phase 2
0.6612	Remote Similarity	NPD7229	Phase 3
0.6612	Remote Similarity	NPD5711	Approved
0.6612	Remote Similarity	NPD5710	Approved
0.6607	Remote Similarity	NPD7097	Phase 1
0.6606	Remote Similarity	NPD6798	Discontinued
0.6606	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3764	Approved
0.6605	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2797	Approved
0.6605	Remote Similarity	NPD3267	Approved
0.6605	Remote Similarity	NPD3266	Approved
0.6588	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6004	Phase 3
0.6588	Remote Similarity	NPD6005	Phase 3
0.6588	Remote Similarity	NPD6002	Phase 3
0.6587	Remote Similarity	NPD4665	Approved
0.6584	Remote Similarity	NPD7701	Phase 2
0.6583	Remote Similarity	NPD3057	Approved
0.6582	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.657	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7003	Approved
0.6569	Remote Similarity	NPD7801	Approved
0.6568	Remote Similarity	NPD3748	Approved
0.6566	Remote Similarity	NPD6233	Phase 2
0.6557	Remote Similarity	NPD7199	Phase 2
0.6552	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1511	Approved
0.6548	Remote Similarity	NPD1607	Approved
0.6545	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5953	Discontinued
0.6541	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4482	Phase 3
0.6532	Remote Similarity	NPD2354	Approved
0.6528	Remote Similarity	NPD8435	Approved
0.6528	Remote Similarity	NPD8360	Approved
0.6528	Remote Similarity	NPD8361	Approved
0.6527	Remote Similarity	NPD1240	Approved
0.6527	Remote Similarity	NPD4060	Phase 1
0.6524	Remote Similarity	NPD7286	Phase 2
0.6522	Remote Similarity	NPD9717	Approved
0.6519	Remote Similarity	NPD7058	Phase 2
0.6519	Remote Similarity	NPD7057	Phase 3
0.651	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1203	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