NPASS Compound

Structure

CID110989 OpenBabel06191715462D 26 28 0 0 1 0 0 0 0 0999 V2000 2.0464 -4.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8825 -5.7916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9481 1.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2611 -2.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9624 -1.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0928 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4722 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7187 -4.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8825 -4.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5291 0.6683 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3476 -1.5231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1311 -0.0865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7451 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7187 -3.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1765 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5636 0.6683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9616 -0.0865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0464 -1.4468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3795 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9163 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8317 -2.4847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5549 -2.8951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1447 1.5382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3208 -1.1027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0464 -2.4123 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 9 1 0 0 0 0 2 9 1 0 0 0 0 5 20 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 10 3 1 1 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 4 1 6 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 6 0 0 0 13 20 1 0 0 0 0 13 21 2 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	2.04
LogD:	1.361
LogS:	-3.144
# Rotatable Bonds:	3
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.459
Synthetic Accessibility Score:	5.024
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.698
MDCK Permeability:	4.1763021727092564e-05
Pgp-inhibitor:	0.886
Pgp-substrate:	0.934
Human Intestinal Absorption (HIA):	0.429
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	40.423789978027344%
Volume Distribution (VD):	0.978
Pgp-substrate:	42.2355842590332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.203
CYP1A2-substrate:	0.272
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.089
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.72
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	12.257
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.413
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.666
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.133
Carcinogencity:	0.204
Eye Corrosion:	0.679
Eye Irritation:	0.123
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC110989

Natural Product ID:	NPC110989
*Common Name:**	Fastigiliin B
IUPAC Name:	[(1S,3aS,4R,5S,5aS,8aR,9S,9aS)-4-hydroxy-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	DLISCHVYLYGCNV-HJDABSCOSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-9(2)8-14(22)25-18-15-11(4)19(24)26-17(15)16(23)10(3)12-6-7-13(21)20(12,18)5/h6-8,10-12,15-18,23H,1-5H3/t10-,11-,12-,15+,16+,17-,18-,20-/m0/s1
SMILES:	CC(=CC(=O)O[C@H]1[C@@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]([C@H]([C@H]2[C@@]1(C)C(=O)C=C2)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1213003
PubChem CID:	442241
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

*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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25440	Phormium tenax	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25440	Phormium tenax	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25440	Phormium tenax	Species	Asphodelaceae	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	3

Activity Type	# Activity
PROTEIN FAMILY	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25088	PROTEIN FAMILY	Janus Kinase (JAK)	Homo sapiens	Inhibition	>	65.0	%	PMID[480181]
NPT25088	PROTEIN FAMILY	Janus Kinase (JAK)	Homo sapiens	Inhibition	=	25.0	%	PMID[480181]
NPT207	Protein Family	MAP kinase p38	Homo sapiens	Inhibition	=	25.0	%	PMID[480181]

☑ 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 NPC110989 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	234
0.1-0.2	1263
0.2-0.3	4713
0.3-0.4	8220
0.4-0.5	14265
0.5-0.6	7662
0.6-0.7	4704
0.7-0.8	1460
0.8-0.85	132
0.85-0.9	30
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC203659
0.9895	High Similarity	NPC225353
0.9192	High Similarity	NPC475945
0.9192	High Similarity	NPC475871
0.9175	High Similarity	NPC141191
0.9167	High Similarity	NPC185553
0.9091	High Similarity	NPC474747
0.9072	High Similarity	NPC169205
0.9062	High Similarity	NPC48803
0.9062	High Similarity	NPC90121
0.9062	High Similarity	NPC193645
0.9062	High Similarity	NPC275960
0.899	High Similarity	NPC474742
0.8947	High Similarity	NPC284185
0.8911	High Similarity	NPC100487
0.8911	High Similarity	NPC474741
0.8842	High Similarity	NPC253144
0.88	High Similarity	NPC171759
0.875	High Similarity	NPC74103
0.875	High Similarity	NPC150978
0.875	High Similarity	NPC70595
0.875	High Similarity	NPC123177
0.8737	High Similarity	NPC52198
0.8737	High Similarity	NPC117405
0.8673	High Similarity	NPC304886
0.8641	High Similarity	NPC243998
0.8627	High Similarity	NPC475873
0.8614	High Similarity	NPC472753
0.8586	High Similarity	NPC126156
0.8571	High Similarity	NPC167219
0.8529	High Similarity	NPC149371
0.8529	High Similarity	NPC86077
0.8529	High Similarity	NPC472754
0.85	High Similarity	NPC170143
0.85	High Similarity	NPC108475
0.85	High Similarity	NPC213947
0.8491	Intermediate Similarity	NPC257240
0.8491	Intermediate Similarity	NPC477103
0.8469	Intermediate Similarity	NPC81419
0.8469	Intermediate Similarity	NPC179746
0.8469	Intermediate Similarity	NPC475912
0.8469	Intermediate Similarity	NPC135776
0.8462	Intermediate Similarity	NPC223450
0.8447	Intermediate Similarity	NPC472755
0.8431	Intermediate Similarity	NPC47880
0.8426	Intermediate Similarity	NPC106395
0.8426	Intermediate Similarity	NPC46269
0.8421	Intermediate Similarity	NPC70555
0.8421	Intermediate Similarity	NPC70422
0.8421	Intermediate Similarity	NPC104961
0.8416	Intermediate Similarity	NPC54843
0.84	Intermediate Similarity	NPC142529
0.84	Intermediate Similarity	NPC476009
0.84	Intermediate Similarity	NPC91771
0.8396	Intermediate Similarity	NPC477102
0.8384	Intermediate Similarity	NPC477131
0.8384	Intermediate Similarity	NPC289004
0.8381	Intermediate Similarity	NPC26617
0.8367	Intermediate Similarity	NPC184463
0.8367	Intermediate Similarity	NPC30515
0.8367	Intermediate Similarity	NPC208886
0.8367	Intermediate Similarity	NPC111114
0.8367	Intermediate Similarity	NPC261607
0.8367	Intermediate Similarity	NPC300312
0.8367	Intermediate Similarity	NPC12172
0.8365	Intermediate Similarity	NPC472756
0.8349	Intermediate Similarity	NPC67290
0.8349	Intermediate Similarity	NPC138303
0.8349	Intermediate Similarity	NPC133677
0.8333	Intermediate Similarity	NPC138757
0.8333	Intermediate Similarity	NPC123855
0.8333	Intermediate Similarity	NPC76550
0.8333	Intermediate Similarity	NPC288876
0.8317	Intermediate Similarity	NPC134454
0.8317	Intermediate Similarity	NPC17326
0.8317	Intermediate Similarity	NPC40812
0.8302	Intermediate Similarity	NPC475960
0.83	Intermediate Similarity	NPC471142
0.83	Intermediate Similarity	NPC36954
0.83	Intermediate Similarity	NPC270013
0.83	Intermediate Similarity	NPC475900
0.83	Intermediate Similarity	NPC14961
0.8283	Intermediate Similarity	NPC295204
0.8283	Intermediate Similarity	NPC212486
0.8283	Intermediate Similarity	NPC476300
0.8283	Intermediate Similarity	NPC162205
0.8283	Intermediate Similarity	NPC273579
0.8283	Intermediate Similarity	NPC288240
0.8265	Intermediate Similarity	NPC106510
0.8265	Intermediate Similarity	NPC51004
0.8265	Intermediate Similarity	NPC473619
0.8265	Intermediate Similarity	NPC71533
0.8252	Intermediate Similarity	NPC185141
0.8252	Intermediate Similarity	NPC46998
0.8252	Intermediate Similarity	NPC128733
0.8252	Intermediate Similarity	NPC477950
0.8252	Intermediate Similarity	NPC110443
0.8252	Intermediate Similarity	NPC133907
0.8247	Intermediate Similarity	NPC202672
0.8241	Intermediate Similarity	NPC287311
0.8235	Intermediate Similarity	NPC187761
0.8235	Intermediate Similarity	NPC473326
0.8235	Intermediate Similarity	NPC83895
0.8235	Intermediate Similarity	NPC471144
0.8224	Intermediate Similarity	NPC38154
0.8218	Intermediate Similarity	NPC21302
0.8218	Intermediate Similarity	NPC477921
0.8218	Intermediate Similarity	NPC24956
0.8218	Intermediate Similarity	NPC18019
0.8218	Intermediate Similarity	NPC473859
0.8218	Intermediate Similarity	NPC11396
0.82	Intermediate Similarity	NPC474035
0.82	Intermediate Similarity	NPC81386
0.8198	Intermediate Similarity	NPC475323
0.8198	Intermediate Similarity	NPC471146
0.8198	Intermediate Similarity	NPC471145
0.8182	Intermediate Similarity	NPC133698
0.8182	Intermediate Similarity	NPC473321
0.8182	Intermediate Similarity	NPC131209
0.8165	Intermediate Similarity	NPC258711
0.8165	Intermediate Similarity	NPC35069
0.8163	Intermediate Similarity	NPC295312
0.8163	Intermediate Similarity	NPC32922
0.8163	Intermediate Similarity	NPC168679
0.8163	Intermediate Similarity	NPC307411
0.8163	Intermediate Similarity	NPC12872
0.8148	Intermediate Similarity	NPC5103
0.8137	Intermediate Similarity	NPC477949
0.8137	Intermediate Similarity	NPC311904
0.8131	Intermediate Similarity	NPC308191
0.8125	Intermediate Similarity	NPC33570
0.8125	Intermediate Similarity	NPC161957
0.8125	Intermediate Similarity	NPC21471
0.8119	Intermediate Similarity	NPC477922
0.8119	Intermediate Similarity	NPC475659
0.8113	Intermediate Similarity	NPC54737
0.8113	Intermediate Similarity	NPC179891
0.81	Intermediate Similarity	NPC153590
0.81	Intermediate Similarity	NPC469645
0.81	Intermediate Similarity	NPC308656
0.81	Intermediate Similarity	NPC473263
0.81	Intermediate Similarity	NPC200237
0.81	Intermediate Similarity	NPC60386
0.81	Intermediate Similarity	NPC469692
0.81	Intermediate Similarity	NPC473234
0.81	Intermediate Similarity	NPC473273
0.8095	Intermediate Similarity	NPC472747
0.8095	Intermediate Similarity	NPC472750
0.8095	Intermediate Similarity	NPC4620
0.8091	Intermediate Similarity	NPC209058
0.8081	Intermediate Similarity	NPC62815
0.8081	Intermediate Similarity	NPC129419
0.8081	Intermediate Similarity	NPC473455
0.8081	Intermediate Similarity	NPC474761
0.8081	Intermediate Similarity	NPC476004
0.8081	Intermediate Similarity	NPC473448
0.8077	Intermediate Similarity	NPC150923
0.8077	Intermediate Similarity	NPC476270
0.8077	Intermediate Similarity	NPC164598
0.8077	Intermediate Similarity	NPC201718
0.8077	Intermediate Similarity	NPC474339
0.8061	Intermediate Similarity	NPC153805
0.8058	Intermediate Similarity	NPC308567
0.8058	Intermediate Similarity	NPC187268
0.8058	Intermediate Similarity	NPC255592
0.8058	Intermediate Similarity	NPC261377
0.8056	Intermediate Similarity	NPC273433
0.8056	Intermediate Similarity	NPC47951
0.8039	Intermediate Similarity	NPC476315
0.8037	Intermediate Similarity	NPC477513
0.802	Intermediate Similarity	NPC476267
0.802	Intermediate Similarity	NPC473331
0.802	Intermediate Similarity	NPC198853
0.802	Intermediate Similarity	NPC323008
0.802	Intermediate Similarity	NPC262133
0.802	Intermediate Similarity	NPC121825
0.802	Intermediate Similarity	NPC470013
0.802	Intermediate Similarity	NPC470010
0.8019	Intermediate Similarity	NPC474917
0.8019	Intermediate Similarity	NPC472748
0.8019	Intermediate Similarity	NPC146731
0.8019	Intermediate Similarity	NPC220964
0.8019	Intermediate Similarity	NPC475676
0.8019	Intermediate Similarity	NPC296950
0.8017	Intermediate Similarity	NPC144625
0.8	Intermediate Similarity	NPC286341
0.8	Intermediate Similarity	NPC191339
0.8	Intermediate Similarity	NPC475925
0.8	Intermediate Similarity	NPC189338
0.8	Intermediate Similarity	NPC95290
0.8	Intermediate Similarity	NPC476705
0.7982	Intermediate Similarity	NPC41551
0.7981	Intermediate Similarity	NPC280963
0.798	Intermediate Similarity	NPC474032
0.798	Intermediate Similarity	NPC87306
0.798	Intermediate Similarity	NPC477017
0.798	Intermediate Similarity	NPC477016
0.798	Intermediate Similarity	NPC280612
0.798	Intermediate Similarity	NPC268298
0.798	Intermediate Similarity	NPC473564

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 NPC110989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1870
0.2-0.3	3735
0.3-0.4	2178
0.4-0.5	748
0.5-0.6	276
0.6-0.7	115
0.7-0.8	9
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD1698	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6371	Approved
0.8381	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5282	Discontinued
0.7647	Intermediate Similarity	NPD7983	Approved
0.7549	Intermediate Similarity	NPD5785	Approved
0.7549	Intermediate Similarity	NPD46	Approved
0.7549	Intermediate Similarity	NPD6698	Approved
0.7547	Intermediate Similarity	NPD4225	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7451	Intermediate Similarity	NPD1695	Approved
0.7379	Intermediate Similarity	NPD7838	Discovery
0.7228	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7115	Discovery
0.71	Intermediate Similarity	NPD5209	Approved
0.7083	Intermediate Similarity	NPD6319	Approved
0.7075	Intermediate Similarity	NPD5778	Approved
0.7075	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD1694	Approved
0.7059	Intermediate Similarity	NPD5363	Approved
0.7018	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7492	Approved
0.699	Remote Similarity	NPD5786	Approved
0.6942	Remote Similarity	NPD6054	Approved
0.6935	Remote Similarity	NPD6616	Approved
0.6931	Remote Similarity	NPD6435	Approved
0.6923	Remote Similarity	NPD6053	Discontinued
0.6905	Remote Similarity	NPD7319	Approved
0.6885	Remote Similarity	NPD8515	Approved
0.6885	Remote Similarity	NPD6016	Approved
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD6015	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.688	Remote Similarity	NPD7078	Approved
0.6864	Remote Similarity	NPD4632	Approved
0.6838	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6370	Approved
0.6829	Remote Similarity	NPD5988	Approved
0.6827	Remote Similarity	NPD4249	Approved
0.6825	Remote Similarity	NPD7736	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7507	Approved
0.6786	Remote Similarity	NPD5344	Discontinued
0.6765	Remote Similarity	NPD4270	Approved
0.6765	Remote Similarity	NPD4269	Approved
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4250	Approved
0.6762	Remote Similarity	NPD4251	Approved
0.6757	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD5368	Approved
0.67	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7154	Phase 3
0.6699	Remote Similarity	NPD5362	Discontinued
0.6696	Remote Similarity	NPD7639	Approved
0.6696	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.664	Remote Similarity	NPD8328	Phase 3
0.664	Remote Similarity	NPD7642	Approved
0.6639	Remote Similarity	NPD8297	Approved
0.6638	Remote Similarity	NPD5697	Approved
0.6638	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6614	Remote Similarity	NPD8074	Phase 3
0.6614	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4634	Approved
0.6581	Remote Similarity	NPD6881	Approved
0.6581	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD7839	Suspended
0.6571	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4252	Approved
0.6557	Remote Similarity	NPD6009	Approved
0.6555	Remote Similarity	NPD6649	Approved
0.6555	Remote Similarity	NPD6650	Approved
0.6552	Remote Similarity	NPD6008	Approved
0.6538	Remote Similarity	NPD7260	Phase 2
0.6525	Remote Similarity	NPD6012	Approved
0.6525	Remote Similarity	NPD6014	Approved
0.6525	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD7637	Suspended
0.6508	Remote Similarity	NPD7830	Approved
0.6508	Remote Similarity	NPD7829	Approved
0.648	Remote Similarity	NPD5983	Phase 2
0.6471	Remote Similarity	NPD6883	Approved
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6442	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7320	Approved
0.6441	Remote Similarity	NPD6011	Approved
0.6417	Remote Similarity	NPD6847	Approved
0.6417	Remote Similarity	NPD8130	Phase 1
0.6417	Remote Similarity	NPD6869	Approved
0.6417	Remote Similarity	NPD6617	Approved
0.641	Remote Similarity	NPD7128	Approved
0.641	Remote Similarity	NPD6675	Approved
0.641	Remote Similarity	NPD5739	Approved
0.641	Remote Similarity	NPD6402	Approved
0.6408	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6648	Approved
0.6387	Remote Similarity	NPD6372	Approved
0.6387	Remote Similarity	NPD6373	Approved
0.6381	Remote Similarity	NPD6110	Phase 1
0.6378	Remote Similarity	NPD7604	Phase 2
0.6371	Remote Similarity	NPD7641	Discontinued
0.6364	Remote Similarity	NPD6845	Suspended
0.6364	Remote Similarity	NPD6882	Approved
0.6356	Remote Similarity	NPD5701	Approved
0.6356	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8444	Approved
0.6349	Remote Similarity	NPD6921	Approved
0.6306	Remote Similarity	NPD6399	Phase 3
0.6293	Remote Similarity	NPD5211	Phase 2
0.6279	Remote Similarity	NPD6336	Discontinued
0.6279	Remote Similarity	NPD8273	Phase 1
0.6279	Remote Similarity	NPD8451	Approved
0.6261	Remote Similarity	NPD5285	Approved
0.6261	Remote Similarity	NPD4696	Approved
0.6261	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4819	Approved
0.624	Remote Similarity	NPD7328	Approved
0.624	Remote Similarity	NPD7327	Approved
0.6231	Remote Similarity	NPD8448	Approved
0.6228	Remote Similarity	NPD6083	Phase 2
0.6228	Remote Similarity	NPD7902	Approved
0.6228	Remote Similarity	NPD6084	Phase 2
0.622	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7503	Approved
0.6216	Remote Similarity	NPD6079	Approved
0.6214	Remote Similarity	NPD4271	Approved
0.6214	Remote Similarity	NPD4268	Approved
0.6212	Remote Similarity	NPD5956	Approved
0.6195	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD7516	Approved
0.6186	Remote Similarity	NPD5141	Approved
0.6183	Remote Similarity	NPD6033	Approved
0.6174	Remote Similarity	NPD5696	Approved
0.616	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD5224	Approved
0.6154	Remote Similarity	NPD7632	Discontinued
0.6148	Remote Similarity	NPD2204	Approved
0.6142	Remote Similarity	NPD8294	Approved
0.6142	Remote Similarity	NPD8377	Approved
0.614	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5221	Approved
0.614	Remote Similarity	NPD5222	Approved
0.6116	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7748	Approved
0.6102	Remote Similarity	NPD5174	Approved
0.6102	Remote Similarity	NPD5175	Approved
0.6094	Remote Similarity	NPD8380	Approved
0.6094	Remote Similarity	NPD8296	Approved
0.6094	Remote Similarity	NPD8268	Approved
0.6094	Remote Similarity	NPD8267	Approved
0.6094	Remote Similarity	NPD8335	Approved
0.6094	Remote Similarity	NPD8266	Approved
0.6094	Remote Similarity	NPD8378	Approved
0.6094	Remote Similarity	NPD8033	Approved
0.6094	Remote Similarity	NPD8379	Approved
0.6094	Remote Similarity	NPD8269	Approved
0.6091	Remote Similarity	NPD6903	Approved
0.609	Remote Similarity	NPD8390	Approved
0.609	Remote Similarity	NPD8392	Approved
0.609	Remote Similarity	NPD8391	Approved
0.6087	Remote Similarity	NPD5173	Approved
0.6087	Remote Similarity	NPD4755	Approved
0.608	Remote Similarity	NPD6274	Approved
0.6078	Remote Similarity	NPD8039	Approved
0.6077	Remote Similarity	NPD8340	Approved
0.6077	Remote Similarity	NPD8299	Approved
0.6077	Remote Similarity	NPD8341	Approved
0.6077	Remote Similarity	NPD8342	Approved
0.6075	Remote Similarity	NPD5331	Approved
0.6075	Remote Similarity	NPD5332	Approved
0.6071	Remote Similarity	NPD5284	Approved
0.6071	Remote Similarity	NPD5281	Approved
0.6071	Remote Similarity	NPD7515	Phase 2
0.6068	Remote Similarity	NPD5223	Approved
0.6063	Remote Similarity	NPD7100	Approved
0.6063	Remote Similarity	NPD7101	Approved
0.6055	Remote Similarity	NPD7334	Approved
0.6055	Remote Similarity	NPD6409	Approved
0.6055	Remote Similarity	NPD5330	Approved
0.6055	Remote Similarity	NPD6684	Approved
0.6055	Remote Similarity	NPD3618	Phase 1
0.6055	Remote Similarity	NPD7146	Approved
0.6055	Remote Similarity	NPD7521	Approved
0.6053	Remote Similarity	NPD5210	Approved
0.6053	Remote Similarity	NPD4629	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