NPASS Compound

Structure

CID306041 OpenBabel06191716112D 29 31 0 0 1 0 0 0 0 0999 V2000 5.9302 -3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7891 0.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6629 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5290 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2562 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2666 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4745 -0.6399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5235 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8109 0.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0678 0.2737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2018 0.7737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4042 1.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9042 2.7224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4097 1.7518 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 11 1 0 0 0 0 2 12 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 2 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 8 13 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 27 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 14 7 1 6 0 0 0 14 15 1 0 0 0 0 15 8 1 1 0 0 0 15 28 1 0 0 0 0 16 9 1 6 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 1 0 0 0 18 19 1 0 0 0 0 18 24 1 6 0 0 0 19 21 1 0 0 0 0 19 25 1 1 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 27 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.19
Volume:	405.879
LogP:	0.545
LogD:	0.806
LogS:	-2.654
# Rotatable Bonds:	4
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	5.122
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.35
MDCK Permeability:	4.3364900193409994e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.956
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.346
Plasma Protein Binding (PPB):	66.83232116699219%
Volume Distribution (VD):	1.147
Pgp-substrate:	23.018537521362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	1.903
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.298
AMES Toxicity:	0.331
Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.716
Carcinogencity:	0.302
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC306041

Natural Product ID:	NPC306041
*Common Name:**	Pirciside B
IUPAC Name:	(3aS,6E,10Z,11aR)-6-methyl-3-methylidene-10-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
Synonyms:
Standard InCHIKey:	OEDNDLHBXUIYOG-VXBUZGHMSA-N
Standard InCHI:	InChI=1S/C21H30O8/c1-11-4-3-5-13(8-15-14(7-6-11)12(2)20(26)28-15)10-27-21-19(25)18(24)17(23)16(9-22)29-21/h4,8,14-19,21-25H,2-3,5-7,9-10H2,1H3/b11-4+,13-8-/t14-,15+,16+,17+,18-,19+,21+/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC/C/2=C[C@H]3OC(=O)C(=C)[C@@H]3CC/C(=C/CC2)/C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622768
PubChem CID:	21636024
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32813	ixeris dentata	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[26341134]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12407	Herba cichorii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2434	Lipotriche scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4151	Rhamnus wightii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	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
Others	4

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	20.1	uM	PMID[490358]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	18.0	uM	PMID[490358]
NPT27	Others	Unspecified		Activity	=	104.7	%	PMID[490358]
NPT27	Others	Unspecified		Activity	=	102.8	%	PMID[490358]

☑ 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 NPC306041 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	177
0.1-0.2	1178
0.2-0.3	4765
0.3-0.4	10207
0.4-0.5	12410
0.5-0.6	7687
0.6-0.7	5001
0.7-0.8	1174
0.8-0.85	87
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9348	High Similarity	NPC54731
0.8804	High Similarity	NPC473619
0.871	High Similarity	NPC473321
0.871	High Similarity	NPC9447
0.8632	High Similarity	NPC471141
0.8602	High Similarity	NPC474232
0.8587	High Similarity	NPC473715
0.8571	High Similarity	NPC473332
0.8511	High Similarity	NPC472197
0.8485	Intermediate Similarity	NPC261117
0.8485	Intermediate Similarity	NPC310804
0.8438	Intermediate Similarity	NPC471142
0.8421	Intermediate Similarity	NPC162205
0.8421	Intermediate Similarity	NPC472195
0.8421	Intermediate Similarity	NPC288240
0.8421	Intermediate Similarity	NPC238090
0.8421	Intermediate Similarity	NPC320089
0.8421	Intermediate Similarity	NPC273579
0.8421	Intermediate Similarity	NPC472196
0.8421	Intermediate Similarity	NPC295204
0.8404	Intermediate Similarity	NPC118078
0.8384	Intermediate Similarity	NPC298255
0.8384	Intermediate Similarity	NPC28304
0.837	Intermediate Similarity	NPC469910
0.8367	Intermediate Similarity	NPC471144
0.8367	Intermediate Similarity	NPC472015
0.8351	Intermediate Similarity	NPC279621
0.8351	Intermediate Similarity	NPC477921
0.8333	Intermediate Similarity	NPC159698
0.83	Intermediate Similarity	NPC250545
0.8298	Intermediate Similarity	NPC474032
0.8283	Intermediate Similarity	NPC475949
0.8283	Intermediate Similarity	NPC255677
0.8283	Intermediate Similarity	NPC22149
0.8283	Intermediate Similarity	NPC306344
0.8265	Intermediate Similarity	NPC472290
0.8261	Intermediate Similarity	NPC21469
0.8247	Intermediate Similarity	NPC477922
0.8247	Intermediate Similarity	NPC36954
0.8242	Intermediate Similarity	NPC169575
0.8242	Intermediate Similarity	NPC116543
0.8242	Intermediate Similarity	NPC473390
0.8242	Intermediate Similarity	NPC131669
0.8242	Intermediate Similarity	NPC40746
0.8229	Intermediate Similarity	NPC61201
0.8229	Intermediate Similarity	NPC476300
0.8229	Intermediate Similarity	NPC475912
0.8222	Intermediate Similarity	NPC24417
0.8211	Intermediate Similarity	NPC6414
0.8211	Intermediate Similarity	NPC475855
0.8211	Intermediate Similarity	NPC303451
0.8202	Intermediate Similarity	NPC98557
0.8202	Intermediate Similarity	NPC167881
0.8191	Intermediate Similarity	NPC137368
0.8191	Intermediate Similarity	NPC475819
0.8191	Intermediate Similarity	NPC476803
0.8182	Intermediate Similarity	NPC279561
0.8182	Intermediate Similarity	NPC249171
0.8182	Intermediate Similarity	NPC49833
0.8182	Intermediate Similarity	NPC187268
0.8163	Intermediate Similarity	NPC473859
0.8152	Intermediate Similarity	NPC288471
0.8152	Intermediate Similarity	NPC266718
0.8152	Intermediate Similarity	NPC476804
0.8152	Intermediate Similarity	NPC158756
0.8144	Intermediate Similarity	NPC474247
0.8144	Intermediate Similarity	NPC71589
0.8144	Intermediate Similarity	NPC57405
0.8144	Intermediate Similarity	NPC303942
0.8137	Intermediate Similarity	NPC474917
0.8137	Intermediate Similarity	NPC86095
0.8132	Intermediate Similarity	NPC229825
0.8125	Intermediate Similarity	NPC184463
0.8125	Intermediate Similarity	NPC30515
0.8125	Intermediate Similarity	NPC472199
0.8119	Intermediate Similarity	NPC222062
0.8119	Intermediate Similarity	NPC13171
0.8119	Intermediate Similarity	NPC195510
0.8081	Intermediate Similarity	NPC304445
0.8081	Intermediate Similarity	NPC236580
0.8077	Intermediate Similarity	NPC177524
0.8077	Intermediate Similarity	NPC475960
0.8077	Intermediate Similarity	NPC219900
0.8077	Intermediate Similarity	NPC392
0.8065	Intermediate Similarity	NPC470755
0.8065	Intermediate Similarity	NPC255307
0.8061	Intermediate Similarity	NPC270013
0.8061	Intermediate Similarity	NPC14961
0.8061	Intermediate Similarity	NPC475659
0.8043	Intermediate Similarity	NPC59097
0.8041	Intermediate Similarity	NPC212486
0.8041	Intermediate Similarity	NPC475838
0.8041	Intermediate Similarity	NPC473663
0.8041	Intermediate Similarity	NPC475173
0.8041	Intermediate Similarity	NPC473561
0.8041	Intermediate Similarity	NPC473723
0.8041	Intermediate Similarity	NPC81419
0.8041	Intermediate Similarity	NPC228451
0.8041	Intermediate Similarity	NPC125674
0.8041	Intermediate Similarity	NPC179746
0.8039	Intermediate Similarity	NPC284929
0.8039	Intermediate Similarity	NPC118761
0.8039	Intermediate Similarity	NPC267869
0.8039	Intermediate Similarity	NPC234304
0.8039	Intermediate Similarity	NPC473148
0.8039	Intermediate Similarity	NPC197541
0.8021	Intermediate Similarity	NPC80875
0.8021	Intermediate Similarity	NPC144133
0.8021	Intermediate Similarity	NPC51004
0.8021	Intermediate Similarity	NPC179394
0.8021	Intermediate Similarity	NPC473904
0.8	Intermediate Similarity	NPC20339
0.8	Intermediate Similarity	NPC203627
0.8	Intermediate Similarity	NPC233551
0.8	Intermediate Similarity	NPC280621
0.8	Intermediate Similarity	NPC48338
0.8	Intermediate Similarity	NPC202672
0.8	Intermediate Similarity	NPC476805
0.8	Intermediate Similarity	NPC40376
0.8	Intermediate Similarity	NPC473326
0.8	Intermediate Similarity	NPC21208
0.798	Intermediate Similarity	NPC476315
0.798	Intermediate Similarity	NPC241911
0.798	Intermediate Similarity	NPC230800
0.7979	Intermediate Similarity	NPC305475
0.7979	Intermediate Similarity	NPC475461
0.7979	Intermediate Similarity	NPC47937
0.7978	Intermediate Similarity	NPC141789
0.7978	Intermediate Similarity	NPC171204
0.7978	Intermediate Similarity	NPC476028
0.7959	Intermediate Similarity	NPC472198
0.7959	Intermediate Similarity	NPC474035
0.7959	Intermediate Similarity	NPC81386
0.7959	Intermediate Similarity	NPC256368
0.7957	Intermediate Similarity	NPC141193
0.7957	Intermediate Similarity	NPC114979
0.7957	Intermediate Similarity	NPC96259
0.7957	Intermediate Similarity	NPC191476
0.7957	Intermediate Similarity	NPC475035
0.7941	Intermediate Similarity	NPC149371
0.7941	Intermediate Similarity	NPC80144
0.7941	Intermediate Similarity	NPC471148
0.7938	Intermediate Similarity	NPC470379
0.7938	Intermediate Similarity	NPC470373
0.7938	Intermediate Similarity	NPC12172
0.7938	Intermediate Similarity	NPC477749
0.7938	Intermediate Similarity	NPC208886
0.7938	Intermediate Similarity	NPC473707
0.7921	Intermediate Similarity	NPC473146
0.7921	Intermediate Similarity	NPC288876
0.7917	Intermediate Similarity	NPC307411
0.7917	Intermediate Similarity	NPC139418
0.79	Intermediate Similarity	NPC476612
0.79	Intermediate Similarity	NPC476613
0.79	Intermediate Similarity	NPC266842
0.7895	Intermediate Similarity	NPC475037
0.7895	Intermediate Similarity	NPC178215
0.7889	Intermediate Similarity	NPC471465
0.7889	Intermediate Similarity	NPC196653
0.7879	Intermediate Similarity	NPC170204
0.7879	Intermediate Similarity	NPC469543
0.7872	Intermediate Similarity	NPC470124
0.7872	Intermediate Similarity	NPC182383
0.7864	Intermediate Similarity	NPC69171
0.7864	Intermediate Similarity	NPC474165
0.7864	Intermediate Similarity	NPC475928
0.7864	Intermediate Similarity	NPC4620
0.7849	Intermediate Similarity	NPC170286
0.7843	Intermediate Similarity	NPC164598
0.7843	Intermediate Similarity	NPC67296
0.7843	Intermediate Similarity	NPC47880
0.7843	Intermediate Similarity	NPC474339
0.7835	Intermediate Similarity	NPC474323
0.7835	Intermediate Similarity	NPC117596
0.7835	Intermediate Similarity	NPC476004
0.7835	Intermediate Similarity	NPC206614
0.7835	Intermediate Similarity	NPC474761
0.7835	Intermediate Similarity	NPC239517
0.7826	Intermediate Similarity	NPC52861
0.781	Intermediate Similarity	NPC477513
0.7802	Intermediate Similarity	NPC270126
0.78	Intermediate Similarity	NPC474297
0.78	Intermediate Similarity	NPC143446
0.7789	Intermediate Similarity	NPC240695
0.7789	Intermediate Similarity	NPC134865
0.7789	Intermediate Similarity	NPC142117
0.7789	Intermediate Similarity	NPC150755
0.7789	Intermediate Similarity	NPC232555
0.7789	Intermediate Similarity	NPC103523
0.7789	Intermediate Similarity	NPC171174
0.7789	Intermediate Similarity	NPC475581
0.7789	Intermediate Similarity	NPC107717
0.7789	Intermediate Similarity	NPC114694
0.7789	Intermediate Similarity	NPC50637
0.7789	Intermediate Similarity	NPC62118
0.7789	Intermediate Similarity	NPC231096
0.7788	Intermediate Similarity	NPC472748
0.7788	Intermediate Similarity	NPC475676
0.7788	Intermediate Similarity	NPC220964
0.7778	Intermediate Similarity	NPC116177

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 NPC306041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1582
0.2-0.3	3876
0.3-0.4	2366
0.4-0.5	761
0.5-0.6	314
0.6-0.7	96
0.7-0.8	9
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
0.8211	Intermediate Similarity	NPD46	Approved
0.8211	Intermediate Similarity	NPD6698	Approved
0.8077	Intermediate Similarity	NPD6686	Approved
0.7685	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8517	Approved
0.7391	Intermediate Similarity	NPD8515	Approved
0.7391	Intermediate Similarity	NPD8513	Phase 3
0.7391	Intermediate Similarity	NPD8516	Approved
0.7315	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7838	Discovery
0.7228	Intermediate Similarity	NPD7983	Approved
0.6983	Remote Similarity	NPD7641	Discontinued
0.6975	Remote Similarity	NPD7830	Approved
0.6975	Remote Similarity	NPD7642	Approved
0.6975	Remote Similarity	NPD7829	Approved
0.6964	Remote Similarity	NPD6371	Approved
0.686	Remote Similarity	NPD7507	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6822	Remote Similarity	NPD4225	Approved
0.6807	Remote Similarity	NPD8444	Approved
0.6803	Remote Similarity	NPD8074	Phase 3
0.6792	Remote Similarity	NPD7839	Suspended
0.6733	Remote Similarity	NPD4249	Approved
0.6721	Remote Similarity	NPD8451	Approved
0.6699	Remote Similarity	NPD1695	Approved
0.6698	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD8448	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6638	Remote Similarity	NPD8133	Approved
0.66	Remote Similarity	NPD7154	Phase 3
0.6579	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7327	Approved
0.6555	Remote Similarity	NPD7328	Approved
0.6545	Remote Similarity	NPD5344	Discontinued
0.6535	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7503	Approved
0.6529	Remote Similarity	NPD8033	Approved
0.6508	Remote Similarity	NPD8390	Approved
0.6508	Remote Similarity	NPD8392	Approved
0.6508	Remote Similarity	NPD8391	Approved
0.6504	Remote Similarity	NPD8342	Approved
0.6504	Remote Similarity	NPD8340	Approved
0.6504	Remote Similarity	NPD8341	Approved
0.6504	Remote Similarity	NPD8299	Approved
0.65	Remote Similarity	NPD7516	Approved
0.6476	Remote Similarity	NPD5785	Approved
0.6465	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5282	Discontinued
0.6446	Remote Similarity	NPD8377	Approved
0.6446	Remote Similarity	NPD8294	Approved
0.6423	Remote Similarity	NPD8328	Phase 3
0.6393	Remote Similarity	NPD8380	Approved
0.6393	Remote Similarity	NPD8296	Approved
0.6393	Remote Similarity	NPD8379	Approved
0.6393	Remote Similarity	NPD8335	Approved
0.6393	Remote Similarity	NPD8378	Approved
0.6355	Remote Similarity	NPD5778	Approved
0.6355	Remote Similarity	NPD5779	Approved
0.6333	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5363	Approved
0.6293	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6110	Phase 1
0.6275	Remote Similarity	NPD5362	Discontinued
0.6271	Remote Similarity	NPD6053	Discontinued
0.6263	Remote Similarity	NPD4271	Approved
0.6263	Remote Similarity	NPD4268	Approved
0.6239	Remote Similarity	NPD6421	Discontinued
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7638	Approved
0.621	Remote Similarity	NPD8080	Discontinued
0.6198	Remote Similarity	NPD7115	Discovery
0.6176	Remote Similarity	NPD6435	Approved
0.6176	Remote Similarity	NPD4270	Approved
0.6176	Remote Similarity	NPD4269	Approved
0.6176	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7639	Approved
0.6161	Remote Similarity	NPD6648	Approved
0.6161	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD1694	Approved
0.6139	Remote Similarity	NPD4822	Approved
0.6139	Remote Similarity	NPD4252	Approved
0.6139	Remote Similarity	NPD4820	Approved
0.6139	Remote Similarity	NPD4821	Approved
0.6139	Remote Similarity	NPD4819	Approved
0.6129	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5786	Approved
0.6094	Remote Similarity	NPD7736	Approved
0.608	Remote Similarity	NPD6370	Approved
0.6078	Remote Similarity	NPD5369	Approved
0.6075	Remote Similarity	NPD6101	Approved
0.6075	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7500	Approved
0.6063	Remote Similarity	NPD8273	Phase 1
0.605	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD8267	Approved
0.6	Remote Similarity	NPD8268	Approved
0.6	Remote Similarity	NPD8269	Approved
0.5984	Remote Similarity	NPD7492	Approved
0.5983	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5368	Approved
0.5963	Remote Similarity	NPD6411	Approved
0.5963	Remote Similarity	NPD7637	Suspended
0.5954	Remote Similarity	NPD7260	Phase 2
0.5941	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6616	Approved
0.5935	Remote Similarity	NPD6009	Approved
0.5932	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6319	Approved
0.592	Remote Similarity	NPD6054	Approved
0.5917	Remote Similarity	NPD2204	Approved
0.5909	Remote Similarity	NPD6399	Phase 3
0.5895	Remote Similarity	NPD897	Approved
0.5895	Remote Similarity	NPD896	Approved
0.5895	Remote Similarity	NPD898	Approved
0.5891	Remote Similarity	NPD7078	Approved
0.5873	Remote Similarity	NPD6016	Approved
0.5873	Remote Similarity	NPD6015	Approved
0.5872	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6882	Approved
0.5865	Remote Similarity	NPD5209	Approved
0.5842	Remote Similarity	NPD4756	Discovery
0.5827	Remote Similarity	NPD5988	Approved
0.582	Remote Similarity	NPD4632	Approved
0.5818	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5331	Approved
0.581	Remote Similarity	NPD5332	Approved
0.58	Remote Similarity	NPD8039	Approved
0.5794	Remote Similarity	NPD6059	Approved
0.5794	Remote Similarity	NPD6422	Discontinued
0.5789	Remote Similarity	NPD6845	Suspended
0.5781	Remote Similarity	NPD6067	Discontinued
0.578	Remote Similarity	NPD5370	Suspended
0.5778	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4790	Discontinued
0.5752	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3197	Phase 1
0.5738	Remote Similarity	NPD969	Suspended
0.5738	Remote Similarity	NPD8297	Approved
0.5729	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD8337	Approved
0.5725	Remote Similarity	NPD8336	Approved
0.5704	Remote Similarity	NPD8415	Approved
0.5684	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7505	Discontinued
0.5669	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6649	Approved
0.5656	Remote Similarity	NPD6650	Approved
0.5655	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8083	Approved
0.5641	Remote Similarity	NPD8082	Approved
0.5641	Remote Similarity	NPD8086	Approved
0.5641	Remote Similarity	NPD8085	Approved
0.5641	Remote Similarity	NPD7632	Discontinued
0.5641	Remote Similarity	NPD8138	Approved
0.5641	Remote Similarity	NPD8084	Approved
0.5641	Remote Similarity	NPD8139	Approved
0.563	Remote Similarity	NPD4211	Phase 1
0.563	Remote Similarity	NPD6008	Approved
0.562	Remote Similarity	NPD6372	Approved
0.562	Remote Similarity	NPD6373	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