NPASS Compound

Structure

CID75724 OpenBabel06191715412D 21 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 18 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.15
Volume:	310.636
LogP:	5.841
LogD:	4.321
LogS:	-4.183
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	3.22
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.922
MDCK Permeability:	1.8585044017527252e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	99.22667694091797%
Volume Distribution (VD):	1.147
Pgp-substrate:	1.5651321411132812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.845
CYP2C19-inhibitor:	0.622
CYP2C19-substrate:	0.168
CYP2C9-inhibitor:	0.687
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.807
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	4.007
Half-life (T1/2):	0.146

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.467
AMES Toxicity:	0.731
Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.96
Carcinogencity:	0.632
Eye Corrosion:	0.011
Eye Irritation:	0.936
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC75724

Natural Product ID:	NPC75724
*Common Name:**	Sibiriquinone A
IUPAC Name:	8,8-dimethyl-2-propan-2-yl-7H-phenanthrene-1,4-dione
Synonyms:
Standard InCHIKey:	QLYRTJYMSVNUFC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O2/c1-11(2)14-10-16(20)17-12-6-5-9-19(3,4)15(12)8-7-13(17)18(14)21/h5-8,10-11H,9H2,1-4H3
SMILES:	CC(C1=CC(=O)c2c(C1=O)ccc1c2C=CCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388964
PubChem CID:	10039317
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	8

Activity Type	# Activity
Cell Line	2
CELL-LINE	2
NON-MOLECULAR	2
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	35700.0	nM	PMID[456645]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	21200.0	nM	PMID[456645]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	340.0	nM	PMID[456645]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	280.0	nM	PMID[456645]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[456645]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	400.0	nM	PMID[456645]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	3500.0	nM	PMID[456645]

☑ 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 NPC75724 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	326
0.1-0.2	1603
0.2-0.3	4183
0.3-0.4	14259
0.4-0.5	14921
0.5-0.6	6214
0.6-0.7	936
0.7-0.8	175
0.8-0.85	41
0.85-0.9	14
0.9-0.95	12
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC134882
0.9674	High Similarity	NPC265220
0.9674	High Similarity	NPC239185
0.967	High Similarity	NPC260233
0.9574	High Similarity	NPC476993
0.9574	High Similarity	NPC109514
0.956	High Similarity	NPC238219
0.9451	High Similarity	NPC155232
0.9451	High Similarity	NPC153885
0.9362	High Similarity	NPC49994
0.9355	High Similarity	NPC185208
0.9355	High Similarity	NPC219573
0.9341	High Similarity	NPC133461
0.9239	High Similarity	NPC1682
0.9239	High Similarity	NPC323420
0.9239	High Similarity	NPC188844
0.9239	High Similarity	NPC59677
0.9231	High Similarity	NPC173413
0.913	High Similarity	NPC284475
0.9011	High Similarity	NPC157778
0.8936	High Similarity	NPC289883
0.8911	High Similarity	NPC470252
0.8901	High Similarity	NPC43945
0.8791	High Similarity	NPC307
0.8791	High Similarity	NPC160339
0.875	High Similarity	NPC470253
0.871	High Similarity	NPC298115
0.8617	High Similarity	NPC277277
0.8617	High Similarity	NPC19256
0.86	High Similarity	NPC247976
0.8511	High Similarity	NPC418308
0.8495	Intermediate Similarity	NPC69057
0.8491	Intermediate Similarity	NPC326664
0.8462	Intermediate Similarity	NPC215008
0.8454	Intermediate Similarity	NPC472880
0.8416	Intermediate Similarity	NPC474866
0.8416	Intermediate Similarity	NPC472691
0.8416	Intermediate Similarity	NPC471829
0.8416	Intermediate Similarity	NPC475939
0.8404	Intermediate Similarity	NPC267262
0.8396	Intermediate Similarity	NPC143768
0.8381	Intermediate Similarity	NPC265513
0.835	Intermediate Similarity	NPC100767
0.8333	Intermediate Similarity	NPC329282
0.8302	Intermediate Similarity	NPC280789
0.8257	Intermediate Similarity	NPC469843
0.8242	Intermediate Similarity	NPC145053
0.8224	Intermediate Similarity	NPC93287
0.8218	Intermediate Similarity	NPC472879
0.8211	Intermediate Similarity	NPC153308
0.8173	Intermediate Similarity	NPC472699
0.8173	Intermediate Similarity	NPC472700
0.8148	Intermediate Similarity	NPC471721
0.8144	Intermediate Similarity	NPC125226
0.8132	Intermediate Similarity	NPC285716
0.8132	Intermediate Similarity	NPC190567
0.8132	Intermediate Similarity	NPC17408
0.8131	Intermediate Similarity	NPC292834
0.8095	Intermediate Similarity	NPC472695
0.8095	Intermediate Similarity	NPC472683
0.8095	Intermediate Similarity	NPC472701
0.8095	Intermediate Similarity	NPC472696
0.8077	Intermediate Similarity	NPC172483
0.8077	Intermediate Similarity	NPC474910
0.8073	Intermediate Similarity	NPC215419
0.8022	Intermediate Similarity	NPC300205
0.8018	Intermediate Similarity	NPC222968
0.8018	Intermediate Similarity	NPC80605
0.8018	Intermediate Similarity	NPC323440
0.8	Intermediate Similarity	NPC164526
0.7963	Intermediate Similarity	NPC218855
0.7959	Intermediate Similarity	NPC103346
0.7935	Intermediate Similarity	NPC164086
0.7912	Intermediate Similarity	NPC285470
0.7912	Intermediate Similarity	NPC103488
0.7912	Intermediate Similarity	NPC2785
0.7912	Intermediate Similarity	NPC36342
0.7895	Intermediate Similarity	NPC252067
0.789	Intermediate Similarity	NPC471481
0.7885	Intermediate Similarity	NPC274443
0.7876	Intermediate Similarity	NPC202015
0.7872	Intermediate Similarity	NPC273758
0.787	Intermediate Similarity	NPC474057
0.787	Intermediate Similarity	NPC137315
0.7857	Intermediate Similarity	NPC58872
0.7849	Intermediate Similarity	NPC12936
0.7849	Intermediate Similarity	NPC273033
0.7818	Intermediate Similarity	NPC130591
0.7818	Intermediate Similarity	NPC234637
0.7802	Intermediate Similarity	NPC245966
0.7788	Intermediate Similarity	NPC318173
0.7788	Intermediate Similarity	NPC244427
0.7788	Intermediate Similarity	NPC222390
0.7767	Intermediate Similarity	NPC221825
0.7755	Intermediate Similarity	NPC325709
0.7755	Intermediate Similarity	NPC113307
0.7748	Intermediate Similarity	NPC217111
0.7748	Intermediate Similarity	NPC474095
0.7748	Intermediate Similarity	NPC93181
0.7745	Intermediate Similarity	NPC226041
0.7745	Intermediate Similarity	NPC240042
0.7742	Intermediate Similarity	NPC71664
0.7736	Intermediate Similarity	NPC471186
0.7692	Intermediate Similarity	NPC128248
0.7692	Intermediate Similarity	NPC328107
0.7692	Intermediate Similarity	NPC133809
0.7692	Intermediate Similarity	NPC225079
0.7692	Intermediate Similarity	NPC136810
0.7685	Intermediate Similarity	NPC192577
0.7684	Intermediate Similarity	NPC197581
0.7684	Intermediate Similarity	NPC39600
0.7679	Intermediate Similarity	NPC260886
0.7677	Intermediate Similarity	NPC303967
0.7677	Intermediate Similarity	NPC67585
0.7677	Intermediate Similarity	NPC110420
0.7658	Intermediate Similarity	NPC67377
0.7636	Intermediate Similarity	NPC186128
0.7634	Intermediate Similarity	NPC139901
0.7634	Intermediate Similarity	NPC151405
0.76	Intermediate Similarity	NPC475023
0.76	Intermediate Similarity	NPC475059
0.7593	Intermediate Similarity	NPC112903
0.7593	Intermediate Similarity	NPC203732
0.7589	Intermediate Similarity	NPC228936
0.7586	Intermediate Similarity	NPC472981
0.7579	Intermediate Similarity	NPC230068
0.757	Intermediate Similarity	NPC134120
0.7565	Intermediate Similarity	NPC476645
0.7547	Intermediate Similarity	NPC329556
0.7544	Intermediate Similarity	NPC61651
0.7544	Intermediate Similarity	NPC268930
0.7525	Intermediate Similarity	NPC475057
0.7524	Intermediate Similarity	NPC112552
0.7521	Intermediate Similarity	NPC167323
0.7521	Intermediate Similarity	NPC269923
0.75	Intermediate Similarity	NPC185763
0.75	Intermediate Similarity	NPC37914
0.75	Intermediate Similarity	NPC83409
0.75	Intermediate Similarity	NPC26224
0.75	Intermediate Similarity	NPC241851
0.75	Intermediate Similarity	NPC238861
0.75	Intermediate Similarity	NPC232958
0.75	Intermediate Similarity	NPC77000
0.7474	Intermediate Similarity	NPC73978
0.7474	Intermediate Similarity	NPC100039
0.7447	Intermediate Similarity	NPC272260
0.7431	Intermediate Similarity	NPC470007
0.7419	Intermediate Similarity	NPC9796
0.7419	Intermediate Similarity	NPC249018
0.7419	Intermediate Similarity	NPC3190
0.7414	Intermediate Similarity	NPC204784
0.7411	Intermediate Similarity	NPC13784
0.7404	Intermediate Similarity	NPC156021
0.7395	Intermediate Similarity	NPC85511
0.7395	Intermediate Similarity	NPC318067
0.7395	Intermediate Similarity	NPC51079
0.7387	Intermediate Similarity	NPC291799
0.7368	Intermediate Similarity	NPC95868
0.7368	Intermediate Similarity	NPC135730
0.7368	Intermediate Similarity	NPC157055
0.7368	Intermediate Similarity	NPC477703
0.7363	Intermediate Similarity	NPC285679
0.7355	Intermediate Similarity	NPC474106
0.735	Intermediate Similarity	NPC476225
0.7345	Intermediate Similarity	NPC196673
0.7345	Intermediate Similarity	NPC196075
0.7339	Intermediate Similarity	NPC142326
0.7339	Intermediate Similarity	NPC94751
0.7333	Intermediate Similarity	NPC145052
0.7328	Intermediate Similarity	NPC472697
0.7328	Intermediate Similarity	NPC472698
0.7321	Intermediate Similarity	NPC66208
0.7321	Intermediate Similarity	NPC471188
0.7321	Intermediate Similarity	NPC471189
0.7295	Intermediate Similarity	NPC51448
0.7295	Intermediate Similarity	NPC115797
0.7295	Intermediate Similarity	NPC478165
0.7295	Intermediate Similarity	NPC478162
0.7288	Intermediate Similarity	NPC144547
0.7281	Intermediate Similarity	NPC186933
0.7264	Intermediate Similarity	NPC54647
0.7263	Intermediate Similarity	NPC159661
0.7253	Intermediate Similarity	NPC74458
0.7245	Intermediate Similarity	NPC267704
0.7238	Intermediate Similarity	NPC133135
0.7238	Intermediate Similarity	NPC251579
0.7234	Intermediate Similarity	NPC179726
0.7232	Intermediate Similarity	NPC95126
0.7232	Intermediate Similarity	NPC475002
0.7203	Intermediate Similarity	NPC472679
0.7203	Intermediate Similarity	NPC472680
0.7203	Intermediate Similarity	NPC289432
0.7203	Intermediate Similarity	NPC988
0.7196	Intermediate Similarity	NPC264728
0.7193	Intermediate Similarity	NPC294458
0.719	Intermediate Similarity	NPC295664
0.7182	Intermediate Similarity	NPC85560
0.7182	Intermediate Similarity	NPC244933
0.7174	Intermediate Similarity	NPC54269
0.7172	Intermediate Similarity	NPC123476

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 NPC75724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	1023
0.2-0.3	1542
0.3-0.4	3303
0.4-0.5	2151
0.5-0.6	671
0.6-0.7	118
0.7-0.8	32
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9674	High Similarity	NPD3495	Discontinued
0.9239	High Similarity	NPD7631	Approved
0.913	High Similarity	NPD7609	Phase 3
0.8901	High Similarity	NPD650	Approved
0.8061	Intermediate Similarity	NPD1508	Approved
0.8037	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD942	Approved
0.7822	Intermediate Similarity	NPD1843	Approved
0.7788	Intermediate Similarity	NPD7009	Phase 2
0.7596	Intermediate Similarity	NPD2066	Phase 3
0.7589	Intermediate Similarity	NPD5951	Approved
0.7586	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1929	Approved
0.7547	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1930	Approved
0.7544	Intermediate Similarity	NPD7610	Discontinued
0.75	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2193	Phase 2
0.7453	Intermediate Similarity	NPD1932	Approved
0.7453	Intermediate Similarity	NPD2648	Phase 3
0.7451	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6049	Phase 2
0.7379	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD2329	Discontinued
0.7364	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2196	Discontinued
0.7257	Intermediate Similarity	NPD6858	Approved
0.7257	Intermediate Similarity	NPD7094	Approved
0.7203	Intermediate Similarity	NPD5836	Discontinued
0.72	Intermediate Similarity	NPD1087	Approved
0.72	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1088	Approved
0.7168	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4879	Approved
0.7048	Intermediate Similarity	NPD1693	Approved
0.7048	Intermediate Similarity	NPD4094	Approved
0.7	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1317	Discontinued
0.699	Remote Similarity	NPD1089	Approved
0.699	Remote Similarity	NPD1090	Approved
0.699	Remote Similarity	NPD1086	Approved
0.6972	Remote Similarity	NPD2171	Approved
0.6937	Remote Similarity	NPD1677	Discontinued
0.6937	Remote Similarity	NPD2197	Approved
0.6937	Remote Similarity	NPD2192	Approved
0.6916	Remote Similarity	NPD4657	Approved
0.6916	Remote Similarity	NPD4655	Approved
0.6911	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2754	Discontinued
0.6893	Remote Similarity	NPD800	Approved
0.6847	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1989	Approved
0.6818	Remote Similarity	NPD6027	Approved
0.6818	Remote Similarity	NPD6024	Approved
0.68	Remote Similarity	NPD3971	Phase 1
0.6797	Remote Similarity	NPD7961	Discontinued
0.6792	Remote Similarity	NPD1563	Approved
0.6783	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3317	Approved
0.6772	Remote Similarity	NPD7008	Discontinued
0.6772	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1099	Approved
0.6759	Remote Similarity	NPD1100	Approved
0.6757	Remote Similarity	NPD3357	Discontinued
0.6754	Remote Similarity	NPD2182	Approved
0.6752	Remote Similarity	NPD7076	Approved
0.6752	Remote Similarity	NPD7077	Approved
0.6748	Remote Similarity	NPD4878	Approved
0.6737	Remote Similarity	NPD4687	Approved
0.6737	Remote Similarity	NPD4058	Approved
0.6729	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD164	Approved
0.6696	Remote Similarity	NPD5909	Discontinued
0.6696	Remote Similarity	NPD664	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6639	Remote Similarity	NPD2932	Approved
0.6614	Remote Similarity	NPD7084	Phase 3
0.6613	Remote Similarity	NPD3972	Approved
0.6606	Remote Similarity	NPD1566	Phase 3
0.6606	Remote Similarity	NPD1564	Approved
0.6606	Remote Similarity	NPD1565	Approved
0.6604	Remote Similarity	NPD1239	Approved
0.6587	Remote Similarity	NPD3245	Phase 3
0.6587	Remote Similarity	NPD3244	Pre-registration
0.6585	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5346	Phase 2
0.6571	Remote Similarity	NPD5347	Phase 2
0.6562	Remote Similarity	NPD5733	Approved
0.6557	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3025	Approved
0.6557	Remote Similarity	NPD3024	Approved
0.6549	Remote Similarity	NPD1237	Approved
0.6532	Remote Similarity	NPD6287	Discontinued
0.6526	Remote Similarity	NPD5276	Approved
0.6518	Remote Similarity	NPD813	Approved
0.6504	Remote Similarity	NPD2345	Approved
0.6504	Remote Similarity	NPD3019	Approved
0.6481	Remote Similarity	NPD1202	Approved
0.6471	Remote Similarity	NPD6010	Discontinued
0.6465	Remote Similarity	NPD227	Approved
0.6465	Remote Similarity	NPD225	Approved
0.6452	Remote Similarity	NPD3026	Approved
0.6452	Remote Similarity	NPD3023	Approved
0.6442	Remote Similarity	NPD9257	Approved
0.6442	Remote Similarity	NPD9259	Approved
0.6434	Remote Similarity	NPD7055	Discontinued
0.6421	Remote Similarity	NPD4691	Approved
0.6417	Remote Similarity	NPD2508	Discontinued
0.6408	Remote Similarity	NPD4544	Approved
0.64	Remote Similarity	NPD9490	Approved
0.6381	Remote Similarity	NPD4793	Discontinued
0.6378	Remote Similarity	NPD1876	Approved
0.6372	Remote Similarity	NPD4803	Discontinued
0.6371	Remote Similarity	NPD4199	Phase 3
0.6339	Remote Similarity	NPD742	Approved
0.6336	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1470	Approved
0.6316	Remote Similarity	NPD4137	Phase 3
0.6316	Remote Similarity	NPD6647	Phase 2
0.6311	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD9491	Approved
0.6304	Remote Similarity	NPD7003	Approved
0.6299	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD3547	Approved
0.6299	Remote Similarity	NPD3549	Approved
0.629	Remote Similarity	NPD1245	Approved
0.6288	Remote Similarity	NPD7713	Phase 3
0.6288	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD2319	Discontinued
0.6275	Remote Similarity	NPD226	Approved
0.627	Remote Similarity	NPD1201	Approved
0.626	Remote Similarity	NPD997	Clinical (unspecified phase)
0.625	Remote Similarity	NPD466	Approved
0.625	Remote Similarity	NPD4747	Approved
0.6216	Remote Similarity	NPD3093	Approved
0.6212	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD9258	Approved
0.6204	Remote Similarity	NPD9256	Approved
0.6195	Remote Similarity	NPD1238	Approved
0.6172	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD9716	Approved
0.616	Remote Similarity	NPD1651	Approved
0.6154	Remote Similarity	NPD4980	Approved
0.6154	Remote Similarity	NPD2798	Approved
0.6148	Remote Similarity	NPD4766	Approved
0.6148	Remote Similarity	NPD1246	Approved
0.6148	Remote Similarity	NPD2629	Approved
0.6143	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6354	Discontinued
0.6134	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3099	Discontinued
0.6129	Remote Similarity	NPD6065	Approved
0.6124	Remote Similarity	NPD2056	Discontinued
0.6116	Remote Similarity	NPD2607	Approved
0.6099	Remote Similarity	NPD7236	Approved
0.6094	Remote Similarity	NPD3355	Approved
0.6094	Remote Similarity	NPD3356	Approved
0.6087	Remote Similarity	NPD2346	Discontinued
0.6077	Remote Similarity	NPD5653	Discontinued
0.6068	Remote Similarity	NPD1763	Approved
0.6068	Remote Similarity	NPD1765	Approved
0.6068	Remote Similarity	NPD1761	Approved
0.6068	Remote Similarity	NPD1766	Approved
0.6068	Remote Similarity	NPD1767	Approved
0.6068	Remote Similarity	NPD1018	Approved
0.6058	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7798	Approved
0.6047	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5157	Phase 1
0.6047	Remote Similarity	NPD5159	Phase 2
0.6036	Remote Similarity	NPD2878	Approved
0.6036	Remote Similarity	NPD3982	Approved
0.6036	Remote Similarity	NPD3980	Approved
0.6034	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD2124	Approved
0.6031	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5598	Approved
0.6018	Remote Similarity	NPD5597	Approved
0.6016	Remote Similarity	NPD1281	Approved
0.6016	Remote Similarity	NPD3867	Phase 2
0.6015	Remote Similarity	NPD6966	Discovery
0.6014	Remote Similarity	NPD5405	Approved
0.6014	Remote Similarity	NPD5406	Approved
0.6014	Remote Similarity	NPD5404	Approved
0.6014	Remote Similarity	NPD5408	Approved
0.6	Remote Similarity	NPD7239	Suspended
0.6	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1752	Approved
0.6	Remote Similarity	NPD4233	Approved
0.6	Remote Similarity	NPD1007	Discontinued
0.6	Remote Similarity	NPD4234	Approved
0.6	Remote Similarity	NPD5991	Approved
0.6	Remote Similarity	NPD1756	Approved
0.6	Remote Similarity	NPD5990	Approved
0.5984	Remote Similarity	NPD4733	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