NPASS Compound

Structure

NPC472691 OpenBabel07101718232D 42 45 0 0 1 0 0 0 0 0999 V2000 -5.6885 3.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7292 5.2984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7415 -4.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4308 -4.0524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3557 -2.6512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2065 -0.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7139 1.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0332 -1.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9054 -1.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2361 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3889 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2361 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7325 3.6514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 4.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7545 3.6748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3889 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4721 -2.6553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2672 2.8631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7579 2.0278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5894 -2.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8194 -1.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9015 0.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2199 4.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -3.6306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7939 -1.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2452 2.8396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2575 -1.1358 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6257 -0.4777 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6945 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1693 0.1613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2758 0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0463 -0.7527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6750 -0.7081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2265 1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5134 -1.2581 0.0000 C 0 0 1 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 1.6945 1.9566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7693 0.4371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3992 1.6468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9520 -1.1223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 35 1 0 0 0 0 9 35 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 24 2 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 17 28 1 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 20 1 0 0 0 0 19 27 2 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 36 1 0 0 0 0 28 31 1 0 0 0 0 29 30 1 0 0 0 0 29 37 1 1 0 0 0 30 23 1 1 0 0 0 30 35 1 0 0 0 0 31 39 2 0 0 0 0 32 36 1 0 0 0 0 32 37 1 0 0 0 0 32 40 2 0 0 0 0 33 36 1 0 0 0 0 33 38 1 0 0 0 0 33 41 2 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 42 2 0 0 0 0 35 38 1 0 0 0 0 36 20 1 1 0 0 0 37 21 1 1 0 0 0 38 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.36
Volume:	637.738
LogP:	9.217
LogD:	6.166
LogS:	-4.216
# Rotatable Bonds:	10
TPSA:	68.28
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.161
Synthetic Accessibility Score:	5.941
Fsp3:	0.526
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.066
MDCK Permeability:	1.751871059241239e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.89
30% Bioavailability (F30%):	0.559

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	89.01567077636719%
Volume Distribution (VD):	2.903
Pgp-substrate:	5.638956546783447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.718
CYP2C19-inhibitor:	0.637
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.939

ADMET: Excretion

Clearance (CL):	13.75
Half-life (T1/2):	0.01

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.514
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.006
Carcinogencity:	0.378
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC472691

Natural Product ID:	NPC472691
*Common Name:**	VMEJLYNTYLRLLY-MASYIOIESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VMEJLYNTYLRLLY-MASYIOIESA-N
Standard InCHI:	InChI=1S/C38H48O4/c1-24(2)14-13-15-27(7)19-20-36-23-30-29(22-26(5)6)37(32(36)40,21-18-25(3)4)34(42)38(33(36)41,35(30,8)9)31(39)28-16-11-10-12-17-28/h10-12,14,16-19,22,29-30H,13,15,20-21,23H2,1-9H3/b27-19+/t29-,30+,36-,37+,38-/m0/s1
SMILES:	CC(=CCCC(=CCC12CC3C(C(C1=O)(C(=O)C(C2=O)(C3(C)C)C(=O)C4=CC=CC=C4)CC=C(C)C)C=C(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581595
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[549024]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[549024]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[549024]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[549024]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[549024]

☑ 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 NPC472691 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	387
0.1-0.2	1577
0.2-0.3	3775
0.3-0.4	12751
0.4-0.5	18134
0.5-0.6	5223
0.6-0.7	744
0.7-0.8	90
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475939
1.0	High Similarity	NPC471829
1.0	High Similarity	NPC474866
0.9208	High Similarity	NPC472696
0.9208	High Similarity	NPC472701
0.9208	High Similarity	NPC472695
0.9208	High Similarity	NPC472683
0.9109	High Similarity	NPC472699
0.9109	High Similarity	NPC472700
0.88	High Similarity	NPC476993
0.88	High Similarity	NPC109514
0.8776	High Similarity	NPC219573
0.8776	High Similarity	NPC185208
0.875	High Similarity	NPC470252
0.8687	High Similarity	NPC239185
0.866	High Similarity	NPC59677
0.86	High Similarity	NPC134882
0.8598	High Similarity	NPC471481
0.8519	High Similarity	NPC130591
0.8519	High Similarity	NPC234637
0.85	High Similarity	NPC265220
0.8482	Intermediate Similarity	NPC472680
0.8482	Intermediate Similarity	NPC472679
0.8469	Intermediate Similarity	NPC188844
0.8469	Intermediate Similarity	NPC1682
0.8469	Intermediate Similarity	NPC323420
0.8416	Intermediate Similarity	NPC75724
0.8378	Intermediate Similarity	NPC268930
0.8367	Intermediate Similarity	NPC284475
0.8333	Intermediate Similarity	NPC218855
0.8304	Intermediate Similarity	NPC472697
0.8304	Intermediate Similarity	NPC472698
0.83	Intermediate Similarity	NPC260233
0.8283	Intermediate Similarity	NPC153885
0.8265	Intermediate Similarity	NPC19256
0.8247	Intermediate Similarity	NPC267262
0.8235	Intermediate Similarity	NPC49994
0.82	Intermediate Similarity	NPC289883
0.82	Intermediate Similarity	NPC238219
0.8198	Intermediate Similarity	NPC260886
0.819	Intermediate Similarity	NPC472681
0.8182	Intermediate Similarity	NPC133461
0.8165	Intermediate Similarity	NPC280789
0.8163	Intermediate Similarity	NPC298115
0.8158	Intermediate Similarity	NPC476225
0.8144	Intermediate Similarity	NPC69057
0.8119	Intermediate Similarity	NPC472880
0.81	Intermediate Similarity	NPC155232
0.8091	Intermediate Similarity	NPC93287
0.8087	Intermediate Similarity	NPC476234
0.8061	Intermediate Similarity	NPC157778
0.8018	Intermediate Similarity	NPC471721
0.7983	Intermediate Similarity	NPC470648
0.7961	Intermediate Similarity	NPC240042
0.7959	Intermediate Similarity	NPC43945
0.7946	Intermediate Similarity	NPC215419
0.7917	Intermediate Similarity	NPC472678
0.7917	Intermediate Similarity	NPC273758
0.7909	Intermediate Similarity	NPC265513
0.7905	Intermediate Similarity	NPC472879
0.79	Intermediate Similarity	NPC173413
0.79	Intermediate Similarity	NPC277277
0.7895	Intermediate Similarity	NPC61651
0.7857	Intermediate Similarity	NPC160339
0.7857	Intermediate Similarity	NPC307
0.7857	Intermediate Similarity	NPC294458
0.7815	Intermediate Similarity	NPC472694
0.7815	Intermediate Similarity	NPC472693
0.78	Intermediate Similarity	NPC418308
0.7789	Intermediate Similarity	NPC477703
0.7789	Intermediate Similarity	NPC164086
0.7789	Intermediate Similarity	NPC190567
0.7768	Intermediate Similarity	NPC470253
0.7708	Intermediate Similarity	NPC145053
0.7708	Intermediate Similarity	NPC273033
0.7708	Intermediate Similarity	NPC12936
0.7685	Intermediate Similarity	NPC329282
0.7684	Intermediate Similarity	NPC300205
0.7652	Intermediate Similarity	NPC469843
0.7647	Intermediate Similarity	NPC125226
0.7607	Intermediate Similarity	NPC202015
0.7604	Intermediate Similarity	NPC285716
0.7604	Intermediate Similarity	NPC71664
0.7604	Intermediate Similarity	NPC17408
0.7593	Intermediate Similarity	NPC247976
0.7583	Intermediate Similarity	NPC325740
0.7579	Intermediate Similarity	NPC285470
0.7579	Intermediate Similarity	NPC2785
0.7579	Intermediate Similarity	NPC36342
0.7563	Intermediate Similarity	NPC269923
0.7563	Intermediate Similarity	NPC167323
0.7551	Intermediate Similarity	NPC215008
0.7545	Intermediate Similarity	NPC100767
0.7544	Intermediate Similarity	NPC326664
0.75	Intermediate Similarity	NPC139901
0.75	Intermediate Similarity	NPC151405
0.75	Intermediate Similarity	NPC272260
0.748	Intermediate Similarity	NPC316553
0.7477	Intermediate Similarity	NPC54647
0.7477	Intermediate Similarity	NPC470007
0.7474	Intermediate Similarity	NPC245966
0.7456	Intermediate Similarity	NPC143768
0.7451	Intermediate Similarity	NPC113307
0.744	Intermediate Similarity	NPC472682
0.744	Intermediate Similarity	NPC472692
0.744	Intermediate Similarity	NPC471334
0.7438	Intermediate Similarity	NPC85511
0.74	Intermediate Similarity	NPC252067
0.7398	Intermediate Similarity	NPC474106
0.7398	Intermediate Similarity	NPC48992
0.7396	Intermediate Similarity	NPC103488
0.7379	Intermediate Similarity	NPC58872
0.736	Intermediate Similarity	NPC25736
0.7353	Intermediate Similarity	NPC153308
0.7317	Intermediate Similarity	NPC294050
0.7317	Intermediate Similarity	NPC328997
0.7317	Intermediate Similarity	NPC470765
0.7315	Intermediate Similarity	NPC221825
0.7308	Intermediate Similarity	NPC103346
0.7297	Intermediate Similarity	NPC471186
0.7295	Intermediate Similarity	NPC328107
0.7292	Intermediate Similarity	NPC179726
0.7292	Intermediate Similarity	NPC9796
0.7288	Intermediate Similarity	NPC94425
0.7288	Intermediate Similarity	NPC80605
0.7288	Intermediate Similarity	NPC222968
0.7288	Intermediate Similarity	NPC323440
0.7282	Intermediate Similarity	NPC325709
0.7273	Intermediate Similarity	NPC329556
0.7258	Intermediate Similarity	NPC146239
0.7258	Intermediate Similarity	NPC470753
0.7258	Intermediate Similarity	NPC473220
0.7252	Intermediate Similarity	NPC471974
0.7252	Intermediate Similarity	NPC469681
0.7252	Intermediate Similarity	NPC469680
0.7248	Intermediate Similarity	NPC128248
0.7248	Intermediate Similarity	NPC136810
0.7248	Intermediate Similarity	NPC133809
0.7245	Intermediate Similarity	NPC95868
0.7241	Intermediate Similarity	NPC67377
0.7238	Intermediate Similarity	NPC475057
0.7236	Intermediate Similarity	NPC478108
0.7232	Intermediate Similarity	NPC244933
0.7232	Intermediate Similarity	NPC85560
0.7217	Intermediate Similarity	NPC186128
0.7217	Intermediate Similarity	NPC292834
0.7212	Intermediate Similarity	NPC67585
0.7212	Intermediate Similarity	NPC110420
0.7212	Intermediate Similarity	NPC303967
0.72	Intermediate Similarity	NPC197581
0.72	Intermediate Similarity	NPC39600
0.7188	Intermediate Similarity	NPC472656
0.7177	Intermediate Similarity	NPC478107
0.7177	Intermediate Similarity	NPC470649
0.7172	Intermediate Similarity	NPC73978
0.7167	Intermediate Similarity	NPC476645
0.7157	Intermediate Similarity	NPC164526
0.7155	Intermediate Similarity	NPC477475
0.7155	Intermediate Similarity	NPC477476
0.7143	Intermediate Similarity	NPC475023
0.7143	Intermediate Similarity	NPC475059
0.713	Intermediate Similarity	NPC226041
0.713	Intermediate Similarity	NPC137315
0.7117	Intermediate Similarity	NPC274443
0.71	Intermediate Similarity	NPC230068
0.7091	Intermediate Similarity	NPC225079
0.7087	Intermediate Similarity	NPC471832
0.7083	Intermediate Similarity	NPC318173
0.7064	Intermediate Similarity	NPC145052
0.7063	Intermediate Similarity	NPC115797
0.7063	Intermediate Similarity	NPC51448
0.7059	Intermediate Similarity	NPC123476
0.7059	Intermediate Similarity	NPC158157
0.7053	Intermediate Similarity	NPC285679
0.7045	Intermediate Similarity	NPC118366
0.7034	Intermediate Similarity	NPC217111
0.7027	Intermediate Similarity	NPC244427
0.7027	Intermediate Similarity	NPC222390
0.7018	Intermediate Similarity	NPC203732
0.7016	Intermediate Similarity	NPC51079
0.7016	Intermediate Similarity	NPC318067
0.7	Intermediate Similarity	NPC203486
0.7	Intermediate Similarity	NPC100039
0.7	Intermediate Similarity	NPC329913
0.7	Intermediate Similarity	NPC126516
0.6991	Remote Similarity	NPC172483
0.6991	Remote Similarity	NPC134120
0.6991	Remote Similarity	NPC474910
0.6991	Remote Similarity	NPC167336
0.6984	Remote Similarity	NPC190849
0.6984	Remote Similarity	NPC171007
0.6983	Remote Similarity	NPC474057
0.6972	Remote Similarity	NPC251579
0.6972	Remote Similarity	NPC133135
0.6972	Remote Similarity	NPC103048
0.6967	Remote Similarity	NPC473243
0.696	Remote Similarity	NPC79698
0.6957	Remote Similarity	NPC192577
0.6947	Remote Similarity	NPC74458
0.6939	Remote Similarity	NPC3190

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 NPC472691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	993
0.2-0.3	1631
0.3-0.4	3585
0.4-0.5	2100
0.5-0.6	449
0.6-0.7	56
0.7-0.8	6
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
0.8687	High Similarity	NPD3495	Discontinued
0.8469	Intermediate Similarity	NPD7631	Approved
0.8367	Intermediate Similarity	NPD7609	Phase 3
0.7959	Intermediate Similarity	NPD650	Approved
0.7895	Intermediate Similarity	NPD7610	Discontinued
0.7745	Intermediate Similarity	NPD1508	Approved
0.7708	Intermediate Similarity	NPD942	Approved
0.7524	Intermediate Similarity	NPD1843	Approved
0.7456	Intermediate Similarity	NPD7094	Approved
0.7456	Intermediate Similarity	NPD6858	Approved
0.7373	Intermediate Similarity	NPD7009	Phase 2
0.7333	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2066	Phase 3
0.7281	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1929	Approved
0.7273	Intermediate Similarity	NPD1930	Approved
0.7273	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7961	Discontinued
0.7179	Intermediate Similarity	NPD5951	Approved
0.717	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1932	Approved
0.7027	Intermediate Similarity	NPD2193	Phase 2
0.7027	Intermediate Similarity	NPD2648	Phase 3
0.6967	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5836	Discontinued
0.6957	Remote Similarity	NPD2329	Discontinued
0.6944	Remote Similarity	NPD6049	Phase 2
0.6944	Remote Similarity	NPD4094	Approved
0.6944	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4879	Approved
0.6875	Remote Similarity	NPD2196	Discontinued
0.6829	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4657	Approved
0.6818	Remote Similarity	NPD4655	Approved
0.6762	Remote Similarity	NPD1087	Approved
0.6759	Remote Similarity	NPD1088	Approved
0.6731	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6024	Approved
0.6726	Remote Similarity	NPD2171	Approved
0.6726	Remote Similarity	NPD6027	Approved
0.6692	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD7076	Approved
0.6667	Remote Similarity	NPD7077	Approved
0.6639	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1693	Approved
0.6613	Remote Similarity	NPD3025	Approved
0.6613	Remote Similarity	NPD3024	Approved
0.661	Remote Similarity	NPD1317	Discontinued
0.6609	Remote Similarity	NPD5909	Discontinued
0.6609	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7713	Phase 3
0.6577	Remote Similarity	NPD1989	Approved
0.6574	Remote Similarity	NPD1086	Approved
0.6574	Remote Similarity	NPD1090	Approved
0.6574	Remote Similarity	NPD1089	Approved
0.6565	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2197	Approved
0.6552	Remote Similarity	NPD2192	Approved
0.6552	Remote Similarity	NPD1677	Discontinued
0.6549	Remote Similarity	NPD7798	Approved
0.6545	Remote Similarity	NPD1202	Approved
0.6545	Remote Similarity	NPD1563	Approved
0.6538	Remote Similarity	NPD7084	Phase 3
0.6538	Remote Similarity	NPD3971	Phase 1
0.6535	Remote Similarity	NPD3972	Approved
0.6518	Remote Similarity	NPD1099	Approved
0.6518	Remote Similarity	NPD1100	Approved
0.6508	Remote Similarity	NPD3026	Approved
0.6508	Remote Similarity	NPD3023	Approved
0.6481	Remote Similarity	NPD5346	Phase 2
0.6481	Remote Similarity	NPD5347	Phase 2
0.6481	Remote Similarity	NPD800	Approved
0.6466	Remote Similarity	NPD1237	Approved
0.6465	Remote Similarity	NPD4058	Approved
0.6457	Remote Similarity	NPD6287	Discontinued
0.6429	Remote Similarity	NPD3019	Approved
0.6422	Remote Similarity	NPD3672	Approved
0.6422	Remote Similarity	NPD3673	Approved
0.6417	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2182	Approved
0.6383	Remote Similarity	NPD7236	Approved
0.6379	Remote Similarity	NPD3357	Discontinued
0.6379	Remote Similarity	NPD6647	Phase 2
0.6377	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD1566	Phase 3
0.6372	Remote Similarity	NPD1565	Approved
0.6372	Remote Similarity	NPD1564	Approved
0.6364	Remote Similarity	NPD1239	Approved
0.6364	Remote Similarity	NPD7055	Discontinued
0.6357	Remote Similarity	NPD8166	Discontinued
0.6348	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD164	Approved
0.6321	Remote Similarity	NPD4544	Approved
0.6312	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2932	Approved
0.6299	Remote Similarity	NPD2345	Approved
0.6296	Remote Similarity	NPD4793	Discontinued
0.6293	Remote Similarity	NPD4803	Discontinued
0.629	Remote Similarity	NPD3317	Approved
0.6269	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.626	Remote Similarity	NPD1470	Approved
0.625	Remote Similarity	NPD2878	Approved
0.625	Remote Similarity	NPD3982	Approved
0.625	Remote Similarity	NPD3980	Approved
0.6241	Remote Similarity	NPD7003	Approved
0.622	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD227	Approved
0.6214	Remote Similarity	NPD225	Approved
0.621	Remote Similarity	NPD3867	Phase 2
0.6204	Remote Similarity	NPD9257	Approved
0.6204	Remote Similarity	NPD9259	Approved
0.6202	Remote Similarity	NPD1201	Approved
0.6198	Remote Similarity	NPD664	Approved
0.6194	Remote Similarity	NPD2754	Discontinued
0.6183	Remote Similarity	NPD1876	Approved
0.6172	Remote Similarity	NPD4199	Phase 3
0.6164	Remote Similarity	NPD7239	Suspended
0.6162	Remote Similarity	NPD4691	Approved
0.6154	Remote Similarity	NPD813	Approved
0.6154	Remote Similarity	NPD9490	Approved
0.6139	Remote Similarity	NPD4687	Approved
0.6139	Remote Similarity	NPD5733	Approved
0.6124	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7458	Discontinued
0.6121	Remote Similarity	NPD1238	Approved
0.6115	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD3547	Approved
0.6107	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD3549	Approved
0.6103	Remote Similarity	NPD7715	Approved
0.6103	Remote Similarity	NPD8032	Phase 2
0.6103	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7714	Approved
0.6098	Remote Similarity	NPD2124	Approved
0.609	Remote Similarity	NPD2798	Approved
0.608	Remote Similarity	NPD2629	Approved
0.6075	Remote Similarity	NPD9491	Approved
0.6071	Remote Similarity	NPD5404	Approved
0.6071	Remote Similarity	NPD5405	Approved
0.6071	Remote Similarity	NPD1007	Discontinued
0.6071	Remote Similarity	NPD5408	Approved
0.6071	Remote Similarity	NPD5406	Approved
0.6066	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4137	Phase 3
0.6043	Remote Similarity	NPD7541	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD8028	Phase 2
0.6038	Remote Similarity	NPD226	Approved
0.6031	Remote Similarity	NPD6637	Approved
0.6029	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD6273	Approved
0.6015	Remote Similarity	NPD5653	Discontinued
0.6	Remote Similarity	NPD6010	Discontinued
0.6	Remote Similarity	NPD4747	Approved
0.5985	Remote Similarity	NPD5159	Phase 2
0.5985	Remote Similarity	NPD5157	Phase 1
0.5985	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7679	Phase 2
0.5983	Remote Similarity	NPD742	Approved
0.5982	Remote Similarity	NPD9258	Approved
0.5982	Remote Similarity	NPD9256	Approved
0.597	Remote Similarity	NPD4980	Approved
0.597	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD1245	Approved
0.5956	Remote Similarity	NPD6966	Discovery
0.5956	Remote Similarity	NPD6039	Approved
0.5956	Remote Similarity	NPD1190	Approved
0.5954	Remote Similarity	NPD7437	Approved
0.5954	Remote Similarity	NPD7436	Approved
0.5952	Remote Similarity	NPD2508	Discontinued
0.5952	Remote Similarity	NPD4766	Approved
0.5952	Remote Similarity	NPD1246	Approved
0.5941	Remote Similarity	NPD5276	Approved
0.594	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6065	Approved
0.5938	Remote Similarity	NPD5990	Approved
0.5938	Remote Similarity	NPD5991	Approved
0.5932	Remote Similarity	NPD6354	Discontinued
0.5923	Remote Similarity	NPD1727	Approved
0.5922	Remote Similarity	NPD9716	Approved
0.5921	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD1471	Phase 3
0.5912	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5926	Approved
0.5897	Remote Similarity	NPD466	Approved
0.5896	Remote Similarity	NPD3267	Approved
0.5896	Remote Similarity	NPD3266	Approved
0.5896	Remote Similarity	NPD3244	Pre-registration
0.5896	Remote Similarity	NPD3245	Phase 3
0.5891	Remote Similarity	NPD6345	Approved
0.5891	Remote Similarity	NPD6343	Approved
0.589	Remote Similarity	NPD8165	Discontinued
0.5887	Remote Similarity	NPD3644	Approved
0.5887	Remote Similarity	NPD3643	Approved
0.5887	Remote Similarity	NPD3642	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