NPASS Compound

Structure

CID86370 OpenBabel06191715422D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.0226 -2.8899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0429 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8104 -5.1591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0869 -5.8106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4472 0.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3416 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7693 -0.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4186 -3.4110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0701 -2.6874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7693 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7195 -4.3371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0680 -5.0606 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1156 -4.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6719 -4.5395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3689 -5.9867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1853 -3.9322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 1 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 27 1 0 0 0 0 25 33 1 6 0 0 0 27 34 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	523.098
LogP:	4.406
LogD:	3.964
LogS:	-4.553
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	4.912
Fsp3:	0.9
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:	-5.024
MDCK Permeability:	1.29640302475309e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	92.94498443603516%
Volume Distribution (VD):	1.002
Pgp-substrate:	1.5731967687606812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.684
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.457
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	5.007
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.804
Skin Sensitization:	0.071
Carcinogencity:	0.067
Eye Corrosion:	0.004
Eye Irritation:	0.03
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: NPC86370

Natural Product ID:	NPC86370
*Common Name:**	CXFVPKAJKNKSNF-DNRQRXMOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CXFVPKAJKNKSNF-DNRQRXMOSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-18(17-21(31)25(33)27(4,5)34)19-11-15-29(7)20(19)9-10-23-28(6)14-13-24(32)26(2,3)22(28)12-16-30(23,29)8/h18,21-23,25,31,33-34H,9-17H2,1-8H3/t18-,21+,22+,23+,25-,28+,29+,30+/m1/s1
SMILES:	C[C@H](C[C@@H]([C@H](C(C)(C)O)O)O)C1=C2CC[C@H]3[C@@]4(C)CCC(=O)C(C)(C)[C@@H]4CC[C@]3(C)[C@@]2(C)CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632954
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
EC50	1
IC50	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	4630.0	nM	PMID[529400]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	3360.0	nM	PMID[529401]

☑ 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 NPC86370 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	189
0.1-0.2	1476
0.2-0.3	5820
0.3-0.4	15776
0.4-0.5	6930
0.5-0.6	6014
0.6-0.7	5051
0.7-0.8	1377
0.8-0.85	38
0.85-0.9	17
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC469317
0.9506	High Similarity	NPC241875
0.9506	High Similarity	NPC469314
0.9268	High Similarity	NPC469322
0.9059	High Similarity	NPC473166
0.9036	High Similarity	NPC90652
0.8953	High Similarity	NPC274046
0.8953	High Similarity	NPC198074
0.8929	High Similarity	NPC470417
0.8902	High Similarity	NPC473157
0.8837	High Similarity	NPC473167
0.8824	High Similarity	NPC229871
0.8824	High Similarity	NPC469319
0.875	High Similarity	NPC473415
0.875	High Similarity	NPC469329
0.875	High Similarity	NPC37787
0.875	High Similarity	NPC180557
0.875	High Similarity	NPC30677
0.8706	High Similarity	NPC44181
0.8636	High Similarity	NPC473172
0.8605	High Similarity	NPC32830
0.8588	High Similarity	NPC99909
0.8588	High Similarity	NPC138756
0.8539	High Similarity	NPC473170
0.8519	High Similarity	NPC476812
0.85	High Similarity	NPC149249
0.8471	Intermediate Similarity	NPC473168
0.8471	Intermediate Similarity	NPC89077
0.8471	Intermediate Similarity	NPC471737
0.8462	Intermediate Similarity	NPC303777
0.8462	Intermediate Similarity	NPC471784
0.8444	Intermediate Similarity	NPC473164
0.8444	Intermediate Similarity	NPC471777
0.8434	Intermediate Similarity	NPC212083
0.8434	Intermediate Similarity	NPC469325
0.8427	Intermediate Similarity	NPC240617
0.8427	Intermediate Similarity	NPC67831
0.8427	Intermediate Similarity	NPC174051
0.8409	Intermediate Similarity	NPC262870
0.8391	Intermediate Similarity	NPC250592
0.8391	Intermediate Similarity	NPC77263
0.8295	Intermediate Similarity	NPC289213
0.8295	Intermediate Similarity	NPC136801
0.8295	Intermediate Similarity	NPC171441
0.8293	Intermediate Similarity	NPC215843
0.8276	Intermediate Similarity	NPC193360
0.8272	Intermediate Similarity	NPC264602
0.8272	Intermediate Similarity	NPC325946
0.8256	Intermediate Similarity	NPC324063
0.8235	Intermediate Similarity	NPC59453
0.8235	Intermediate Similarity	NPC85774
0.8235	Intermediate Similarity	NPC214043
0.8235	Intermediate Similarity	NPC221758
0.8235	Intermediate Similarity	NPC82902
0.8222	Intermediate Similarity	NPC318332
0.8214	Intermediate Similarity	NPC145143
0.8214	Intermediate Similarity	NPC151519
0.8202	Intermediate Similarity	NPC155304
0.8191	Intermediate Similarity	NPC469316
0.8182	Intermediate Similarity	NPC476733
0.8182	Intermediate Similarity	NPC474245
0.8182	Intermediate Similarity	NPC1015
0.8182	Intermediate Similarity	NPC215029
0.8182	Intermediate Similarity	NPC31985
0.8161	Intermediate Similarity	NPC317590
0.8152	Intermediate Similarity	NPC473161
0.814	Intermediate Similarity	NPC471224
0.814	Intermediate Similarity	NPC474218
0.814	Intermediate Similarity	NPC197823
0.8125	Intermediate Similarity	NPC470299
0.8105	Intermediate Similarity	NPC324001
0.8095	Intermediate Similarity	NPC3915
0.809	Intermediate Similarity	NPC85173
0.809	Intermediate Similarity	NPC320026
0.809	Intermediate Similarity	NPC126993
0.8085	Intermediate Similarity	NPC469327
0.8085	Intermediate Similarity	NPC476897
0.8085	Intermediate Similarity	NPC473174
0.8072	Intermediate Similarity	NPC201459
0.8068	Intermediate Similarity	NPC474677
0.8046	Intermediate Similarity	NPC474732
0.8046	Intermediate Similarity	NPC469994
0.8046	Intermediate Similarity	NPC51014
0.8046	Intermediate Similarity	NPC213412
0.8046	Intermediate Similarity	NPC474778
0.8046	Intermediate Similarity	NPC474733
0.8046	Intermediate Similarity	NPC145879
0.8046	Intermediate Similarity	NPC56588
0.8046	Intermediate Similarity	NPC31564
0.8023	Intermediate Similarity	NPC329043
0.8023	Intermediate Similarity	NPC180834
0.8023	Intermediate Similarity	NPC321187
0.8023	Intermediate Similarity	NPC473246
0.8023	Intermediate Similarity	NPC58841
0.8023	Intermediate Similarity	NPC161423
0.8023	Intermediate Similarity	NPC227064
0.8022	Intermediate Similarity	NPC473162
0.8	Intermediate Similarity	NPC86266
0.8	Intermediate Similarity	NPC189520
0.8	Intermediate Similarity	NPC212301
0.8	Intermediate Similarity	NPC110657
0.8	Intermediate Similarity	NPC473163
0.8	Intermediate Similarity	NPC477858
0.8	Intermediate Similarity	NPC235704
0.8	Intermediate Similarity	NPC310989
0.7979	Intermediate Similarity	NPC473176
0.7979	Intermediate Similarity	NPC167974
0.7978	Intermediate Similarity	NPC469323
0.7978	Intermediate Similarity	NPC475921
0.7978	Intermediate Similarity	NPC310010
0.7978	Intermediate Similarity	NPC76879
0.7978	Intermediate Similarity	NPC474704
0.7978	Intermediate Similarity	NPC477943
0.7978	Intermediate Similarity	NPC326627
0.7978	Intermediate Similarity	NPC122116
0.7978	Intermediate Similarity	NPC2983
0.7976	Intermediate Similarity	NPC2482
0.7957	Intermediate Similarity	NPC474785
0.7957	Intermediate Similarity	NPC474938
0.7955	Intermediate Similarity	NPC475740
0.7955	Intermediate Similarity	NPC251808
0.7955	Intermediate Similarity	NPC58063
0.7955	Intermediate Similarity	NPC93778
0.7955	Intermediate Similarity	NPC96496
0.7955	Intermediate Similarity	NPC474174
0.7938	Intermediate Similarity	NPC470587
0.7935	Intermediate Similarity	NPC200702
0.7931	Intermediate Similarity	NPC274724
0.7931	Intermediate Similarity	NPC470574
0.7931	Intermediate Similarity	NPC474083
0.7931	Intermediate Similarity	NPC469948
0.7931	Intermediate Similarity	NPC133954
0.7917	Intermediate Similarity	NPC239716
0.7912	Intermediate Similarity	NPC118490
0.7912	Intermediate Similarity	NPC141497
0.7912	Intermediate Similarity	NPC275809
0.7912	Intermediate Similarity	NPC107674
0.7912	Intermediate Similarity	NPC474736
0.7912	Intermediate Similarity	NPC141447
0.7912	Intermediate Similarity	NPC170220
0.7907	Intermediate Similarity	NPC215893
0.7907	Intermediate Similarity	NPC476100
0.7907	Intermediate Similarity	NPC475726
0.7907	Intermediate Similarity	NPC472743
0.7901	Intermediate Similarity	NPC472854
0.7889	Intermediate Similarity	NPC46758
0.7889	Intermediate Similarity	NPC49320
0.7882	Intermediate Similarity	NPC474484
0.7882	Intermediate Similarity	NPC103754
0.7872	Intermediate Similarity	NPC191565
0.7865	Intermediate Similarity	NPC255176
0.7865	Intermediate Similarity	NPC292491
0.7865	Intermediate Similarity	NPC328313
0.7865	Intermediate Similarity	NPC53911
0.7865	Intermediate Similarity	NPC310752
0.7865	Intermediate Similarity	NPC230387
0.7857	Intermediate Similarity	NPC473173
0.7857	Intermediate Similarity	NPC473165
0.7857	Intermediate Similarity	NPC474113
0.7857	Intermediate Similarity	NPC469318
0.7857	Intermediate Similarity	NPC471783
0.7857	Intermediate Similarity	NPC9457
0.7849	Intermediate Similarity	NPC473158
0.7849	Intermediate Similarity	NPC471822
0.7849	Intermediate Similarity	NPC49371
0.7849	Intermediate Similarity	NPC471463
0.7841	Intermediate Similarity	NPC74363
0.7841	Intermediate Similarity	NPC322159
0.7841	Intermediate Similarity	NPC70661
0.7841	Intermediate Similarity	NPC475862
0.7841	Intermediate Similarity	NPC73038
0.7841	Intermediate Similarity	NPC20688
0.7841	Intermediate Similarity	NPC80590
0.7841	Intermediate Similarity	NPC475181
0.7841	Intermediate Similarity	NPC158393
0.7841	Intermediate Similarity	NPC475007
0.7841	Intermediate Similarity	NPC72133
0.7841	Intermediate Similarity	NPC327115
0.7841	Intermediate Similarity	NPC155011
0.7831	Intermediate Similarity	NPC476811
0.7831	Intermediate Similarity	NPC472746
0.7831	Intermediate Similarity	NPC106078
0.7826	Intermediate Similarity	NPC8993
0.7826	Intermediate Similarity	NPC263548
0.7826	Intermediate Similarity	NPC299996
0.7826	Intermediate Similarity	NPC282395
0.7826	Intermediate Similarity	NPC145667
0.7826	Intermediate Similarity	NPC209662
0.7826	Intermediate Similarity	NPC49670
0.7826	Intermediate Similarity	NPC32407
0.7826	Intermediate Similarity	NPC20235
0.7826	Intermediate Similarity	NPC231063
0.7826	Intermediate Similarity	NPC88116
0.7816	Intermediate Similarity	NPC171789
0.7816	Intermediate Similarity	NPC474233
0.7816	Intermediate Similarity	NPC227132
0.7816	Intermediate Similarity	NPC237712
0.7816	Intermediate Similarity	NPC474482
0.7816	Intermediate Similarity	NPC475745
0.7812	Intermediate Similarity	NPC473928

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 NPC86370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1906
0.2-0.3	4025
0.3-0.4	2122
0.4-0.5	499
0.5-0.6	169
0.6-0.7	206
0.7-0.8	59
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
0.8235	Intermediate Similarity	NPD4786	Approved
0.8214	Intermediate Similarity	NPD3667	Approved
0.8023	Intermediate Similarity	NPD3133	Approved
0.8023	Intermediate Similarity	NPD3665	Phase 1
0.8023	Intermediate Similarity	NPD3666	Approved
0.7978	Intermediate Similarity	NPD4753	Phase 2
0.7907	Intermediate Similarity	NPD4788	Approved
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD5328	Approved
0.775	Intermediate Similarity	NPD4245	Approved
0.775	Intermediate Similarity	NPD4244	Approved
0.7738	Intermediate Similarity	NPD3617	Approved
0.7654	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3698	Phase 2
0.7625	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3668	Phase 3
0.7609	Intermediate Similarity	NPD6079	Approved
0.7609	Intermediate Similarity	NPD7515	Phase 2
0.7586	Intermediate Similarity	NPD4223	Phase 3
0.7586	Intermediate Similarity	NPD4221	Approved
0.7579	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD4755	Approved
0.7579	Intermediate Similarity	NPD6083	Phase 2
0.7558	Intermediate Similarity	NPD7525	Registered
0.7553	Intermediate Similarity	NPD4629	Approved
0.7553	Intermediate Similarity	NPD5210	Approved
0.7531	Intermediate Similarity	NPD4789	Approved
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5329	Approved
0.7527	Intermediate Similarity	NPD4202	Approved
0.7527	Intermediate Similarity	NPD6399	Phase 3
0.7471	Intermediate Similarity	NPD4692	Approved
0.7471	Intermediate Similarity	NPD4139	Approved
0.7444	Intermediate Similarity	NPD5279	Phase 3
0.7444	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4700	Approved
0.7423	Intermediate Similarity	NPD4696	Approved
0.7423	Intermediate Similarity	NPD5285	Approved
0.7423	Intermediate Similarity	NPD5286	Approved
0.7416	Intermediate Similarity	NPD4197	Approved
0.7342	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6412	Phase 2
0.7294	Intermediate Similarity	NPD6933	Approved
0.7294	Intermediate Similarity	NPD6117	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4697	Phase 3
0.7284	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5360	Phase 3
0.7283	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7263	Intermediate Similarity	NPD7748	Approved
0.7262	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4688	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD4689	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD4138	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD4623	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD4519	Discontinued
0.7253	Intermediate Similarity	NPD4693	Phase 3
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD5205	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7253	Intermediate Similarity	NPD4690	Approved
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7209	Intermediate Similarity	NPD6116	Phase 1
0.72	Intermediate Similarity	NPD5175	Approved
0.72	Intermediate Similarity	NPD5174	Approved
0.7195	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5695	Phase 3
0.7176	Intermediate Similarity	NPD6942	Approved
0.7176	Intermediate Similarity	NPD3703	Phase 2
0.7176	Intermediate Similarity	NPD7339	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7159	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD5696	Approved
0.7129	Intermediate Similarity	NPD5141	Approved
0.7126	Intermediate Similarity	NPD6114	Approved
0.7126	Intermediate Similarity	NPD6697	Approved
0.7126	Intermediate Similarity	NPD6118	Approved
0.7126	Intermediate Similarity	NPD6115	Approved
0.7115	Intermediate Similarity	NPD4634	Approved
0.7097	Intermediate Similarity	NPD6672	Approved
0.7097	Intermediate Similarity	NPD5737	Approved
0.7097	Intermediate Similarity	NPD6903	Approved
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD7320	Approved
0.7087	Intermediate Similarity	NPD6881	Approved
0.7065	Intermediate Similarity	NPD5280	Approved
0.7065	Intermediate Similarity	NPD4694	Approved
0.7065	Intermediate Similarity	NPD5690	Phase 2
0.7059	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD4767	Approved
0.7059	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD6926	Approved
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.7045	Intermediate Similarity	NPD7645	Phase 2
0.7041	Intermediate Similarity	NPD7902	Approved
0.703	Intermediate Similarity	NPD4754	Approved
0.7024	Intermediate Similarity	NPD6081	Approved
0.7021	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.699	Remote Similarity	NPD5701	Approved
0.699	Remote Similarity	NPD5697	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6952	Remote Similarity	NPD7290	Approved
0.6952	Remote Similarity	NPD6883	Approved
0.6952	Remote Similarity	NPD7102	Approved
0.6932	Remote Similarity	NPD3671	Phase 1
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD5128	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6887	Remote Similarity	NPD6869	Approved
0.6887	Remote Similarity	NPD8130	Phase 1
0.6887	Remote Similarity	NPD6649	Approved
0.6887	Remote Similarity	NPD6650	Approved
0.6887	Remote Similarity	NPD6617	Approved
0.6887	Remote Similarity	NPD6847	Approved
0.6882	Remote Similarity	NPD6098	Approved
0.6881	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6857	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6014	Approved
0.6857	Remote Similarity	NPD6012	Approved
0.6857	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4195	Approved
0.6842	Remote Similarity	NPD6673	Approved
0.6842	Remote Similarity	NPD6904	Approved
0.6842	Remote Similarity	NPD6080	Approved
0.6829	Remote Similarity	NPD4224	Phase 2
0.6824	Remote Similarity	NPD4758	Discontinued
0.6824	Remote Similarity	NPD5777	Approved
0.6824	Remote Similarity	NPD4243	Approved
0.6822	Remote Similarity	NPD6882	Approved
0.6809	Remote Similarity	NPD7524	Approved
0.6792	Remote Similarity	NPD5250	Approved
0.6792	Remote Similarity	NPD5249	Phase 3
0.6792	Remote Similarity	NPD5251	Approved
0.6792	Remote Similarity	NPD5248	Approved
0.6792	Remote Similarity	NPD5247	Approved
0.6786	Remote Similarity	NPD4137	Phase 3
0.6778	Remote Similarity	NPD6931	Approved
0.6778	Remote Similarity	NPD4748	Discontinued
0.6778	Remote Similarity	NPD6930	Phase 2
0.6778	Remote Similarity	NPD7509	Discontinued
0.6765	Remote Similarity	NPD7632	Discontinued
0.6762	Remote Similarity	NPD6011	Approved
0.6762	Remote Similarity	NPD6686	Approved
0.6759	Remote Similarity	NPD4632	Approved
0.6742	Remote Similarity	NPD5364	Discontinued
0.6742	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6695	Phase 3
0.6735	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7900	Approved
0.6729	Remote Similarity	NPD5215	Approved
0.6729	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5217	Approved
0.6729	Remote Similarity	NPD5216	Approved
0.6707	Remote Similarity	NPD7341	Phase 2
0.6706	Remote Similarity	NPD4747	Approved
0.6706	Remote Similarity	NPD4691	Approved
0.6701	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6929	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5133	Approved
0.6629	Remote Similarity	NPD6932	Approved
0.6607	Remote Similarity	NPD4522	Approved
0.6604	Remote Similarity	NPD5168	Approved
0.66	Remote Similarity	NPD7614	Phase 1
0.6598	Remote Similarity	NPD4096	Approved
0.6593	Remote Similarity	NPD5368	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