NPASS Compound

Structure

CID314727 OpenBabel06191716122D 37 38 0 0 1 0 0 0 0 0999 V2000 -9.2820 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4382 3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7506 3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0629 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4382 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7506 2.9231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2191 2.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9067 2.4359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5944 2.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9067 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5944 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 4.8718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.8718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 21 1 0 0 0 0 11 17 2 0 0 0 0 12 21 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 30 1 0 0 0 0 15 28 1 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 19 6 1 1 0 0 0 19 24 1 0 0 0 0 19 27 1 0 0 0 0 20 7 1 1 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 31 1 6 0 0 0 22 11 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 0 0 0 0 23 32 1 1 0 0 0 24 33 1 6 0 0 0 25 30 1 1 0 0 0 25 34 1 0 0 0 0 26 16 1 1 0 0 0 27 30 1 1 0 0 0 28 35 1 1 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.36
Volume:	561.309
LogP:	3.306
LogD:	2.448
LogS:	-3.867
# Rotatable Bonds:	10
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	5.589
Fsp3:	0.767
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.449
MDCK Permeability:	4.529723082669079e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.838
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	88.32329559326172%
Volume Distribution (VD):	0.475
Pgp-substrate:	5.428769588470459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.464
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	4.132
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.792
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.54
Carcinogencity:	0.007
Eye Corrosion:	0.005
Eye Irritation:	0.023
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC314727

Natural Product ID:	NPC314727
*Common Name:**	Nahuoic Acid
IUPAC Name:	(E)-3-[(1R,2R,4aR,5R,7R,8R,8aS)-5,7-dihydroxy-3,4a,8-trimethyl-2-[(E,5S,7R,8S,9S)-5,7,9-trihydroxy-8,10-dimethylundec-2-en-2-yl]-2,5,6,7,8,8a-hexahydro-1H-naphthalen-1-yl]-2-methylprop-2-enoic acid
Synonyms:
Standard InCHIKey:	ZNAYXHSDZPSFLO-UWXUHECCSA-N
Standard InCHI:	InChI=1S/C30H50O7/c1-15(2)28(35)20(7)23(32)12-21(31)10-9-16(3)26-18(5)14-30(8)25(34)13-24(33)19(6)27(30)22(26)11-17(4)29(36)37/h9,11,14-15,19-28,31-35H,10,12-13H2,1-8H3,(H,36,37)/b16-9+,17-11+/t19-,20-,21-,22-,23+,24+,25+,26+,27+,28-,30+/m0/s1
SMILES:	CC(C)[C@@H]([C@@H](C)[C@@H](C[C@H](C/C=C(C)/[C@@H]1C(=C[C@]2(C)[C@@H](C[C@H]([C@H](C)[C@@H]2[C@H]1/C=C(C)/C(=O)O)O)O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3318284
PubChem CID:	71521340
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO40706	Streptomyces sp. SCSGAA 0027	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26684286]

☑ 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	6
Ki	2
Others	1

Activity Type	# Activity
Individual Protein	8
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	IC50	=	6500.0	nM	PMID[541811]
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	Ki	=	2000.0	nM	PMID[541812]
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	IC50	=	6500.0	nM	PMID[541812]
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	IC50	=	6500.0	nM	PMID[541813]
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	IC50	=	6500.0	nM	PMID[541815]
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	Ki	=	2000.0	nM	PMID[541815]
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	IC50	=	6500.0	nM	PMID[541816]
NPT5900	Individual Protein	N-lysine methyltransferase SETD8	Homo sapiens	IC50	=	6500.0	nM	PMID[541817]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	98.0	%	PMID[541814]

☑ 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 NPC314727 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	181
0.1-0.2	1122
0.2-0.3	4253
0.3-0.4	8200
0.4-0.5	14608
0.5-0.6	6864
0.6-0.7	5544
0.7-0.8	1765
0.8-0.85	134
0.85-0.9	21
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9101	High Similarity	NPC119562
0.9101	High Similarity	NPC279410
0.8837	High Similarity	NPC109528
0.8824	High Similarity	NPC79945
0.881	High Similarity	NPC159148
0.8804	High Similarity	NPC99726
0.875	High Similarity	NPC104560
0.8721	High Similarity	NPC302360
0.8706	High Similarity	NPC256112
0.8706	High Similarity	NPC2524
0.869	High Similarity	NPC281880
0.8652	High Similarity	NPC146554
0.8652	High Similarity	NPC262858
0.8652	High Similarity	NPC472240
0.8605	High Similarity	NPC57370
0.8587	High Similarity	NPC276110
0.8571	High Similarity	NPC214697
0.8556	High Similarity	NPC48732
0.8556	High Similarity	NPC78973
0.8539	High Similarity	NPC7280
0.8539	High Similarity	NPC229612
0.8523	High Similarity	NPC175145
0.8523	High Similarity	NPC475069
0.8523	High Similarity	NPC473226
0.8511	High Similarity	NPC218107
0.8495	Intermediate Similarity	NPC202833
0.8495	Intermediate Similarity	NPC165632
0.8488	Intermediate Similarity	NPC224455
0.8478	Intermediate Similarity	NPC57117
0.8478	Intermediate Similarity	NPC476186
0.8462	Intermediate Similarity	NPC212948
0.8462	Intermediate Similarity	NPC124374
0.8444	Intermediate Similarity	NPC246028
0.8421	Intermediate Similarity	NPC38855
0.8404	Intermediate Similarity	NPC141401
0.8404	Intermediate Similarity	NPC287668
0.8404	Intermediate Similarity	NPC320306
0.8391	Intermediate Similarity	NPC476927
0.8387	Intermediate Similarity	NPC266899
0.8372	Intermediate Similarity	NPC170303
0.837	Intermediate Similarity	NPC99653
0.837	Intermediate Similarity	NPC38232
0.837	Intermediate Similarity	NPC476304
0.8352	Intermediate Similarity	NPC473099
0.8352	Intermediate Similarity	NPC220216
0.8351	Intermediate Similarity	NPC478057
0.8351	Intermediate Similarity	NPC95899
0.8333	Intermediate Similarity	NPC291665
0.8333	Intermediate Similarity	NPC473229
0.8316	Intermediate Similarity	NPC275086
0.8316	Intermediate Similarity	NPC325229
0.8316	Intermediate Similarity	NPC478056
0.83	Intermediate Similarity	NPC475586
0.8298	Intermediate Similarity	NPC114743
0.8298	Intermediate Similarity	NPC221801
0.8298	Intermediate Similarity	NPC190713
0.8298	Intermediate Similarity	NPC134072
0.8298	Intermediate Similarity	NPC211810
0.8298	Intermediate Similarity	NPC284194
0.8298	Intermediate Similarity	NPC195366
0.8298	Intermediate Similarity	NPC471765
0.8298	Intermediate Similarity	NPC234993
0.8295	Intermediate Similarity	NPC102048
0.828	Intermediate Similarity	NPC474922
0.828	Intermediate Similarity	NPC159365
0.8261	Intermediate Similarity	NPC477574
0.8261	Intermediate Similarity	NPC72845
0.8261	Intermediate Similarity	NPC74296
0.8261	Intermediate Similarity	NPC473675
0.8261	Intermediate Similarity	NPC110923
0.8247	Intermediate Similarity	NPC109195
0.8247	Intermediate Similarity	NPC475038
0.8247	Intermediate Similarity	NPC476081
0.8247	Intermediate Similarity	NPC293753
0.8247	Intermediate Similarity	NPC472552
0.8242	Intermediate Similarity	NPC473100
0.8242	Intermediate Similarity	NPC472983
0.8242	Intermediate Similarity	NPC261320
0.8242	Intermediate Similarity	NPC16265
0.8229	Intermediate Similarity	NPC470074
0.8229	Intermediate Similarity	NPC327431
0.8211	Intermediate Similarity	NPC51499
0.8211	Intermediate Similarity	NPC108078
0.8211	Intermediate Similarity	NPC473244
0.8202	Intermediate Similarity	NPC35933
0.8191	Intermediate Similarity	NPC476245
0.8182	Intermediate Similarity	NPC111952
0.8182	Intermediate Similarity	NPC88349
0.8172	Intermediate Similarity	NPC152778
0.8172	Intermediate Similarity	NPC205034
0.8172	Intermediate Similarity	NPC162615
0.8163	Intermediate Similarity	NPC85742
0.8163	Intermediate Similarity	NPC120321
0.8163	Intermediate Similarity	NPC23584
0.8161	Intermediate Similarity	NPC473420
0.8161	Intermediate Similarity	NPC476646
0.8161	Intermediate Similarity	NPC249423
0.8152	Intermediate Similarity	NPC19771
0.8144	Intermediate Similarity	NPC472554
0.8125	Intermediate Similarity	NPC278673
0.8125	Intermediate Similarity	NPC216478
0.8118	Intermediate Similarity	NPC132542
0.8111	Intermediate Similarity	NPC82979
0.8111	Intermediate Similarity	NPC472986
0.8111	Intermediate Similarity	NPC6391
0.8111	Intermediate Similarity	NPC472985
0.8111	Intermediate Similarity	NPC131813
0.8105	Intermediate Similarity	NPC16967
0.8105	Intermediate Similarity	NPC276103
0.8105	Intermediate Similarity	NPC54248
0.8105	Intermediate Similarity	NPC301534
0.8105	Intermediate Similarity	NPC250757
0.81	Intermediate Similarity	NPC143609
0.81	Intermediate Similarity	NPC187435
0.81	Intermediate Similarity	NPC472925
0.81	Intermediate Similarity	NPC67321
0.809	Intermediate Similarity	NPC306951
0.8085	Intermediate Similarity	NPC191521
0.8085	Intermediate Similarity	NPC470957
0.8085	Intermediate Similarity	NPC470958
0.8085	Intermediate Similarity	NPC472360
0.8085	Intermediate Similarity	NPC105490
0.8085	Intermediate Similarity	NPC472416
0.8065	Intermediate Similarity	NPC475708
0.8065	Intermediate Similarity	NPC472978
0.8065	Intermediate Similarity	NPC473944
0.8065	Intermediate Similarity	NPC116726
0.8061	Intermediate Similarity	NPC273668
0.8061	Intermediate Similarity	NPC234892
0.8061	Intermediate Similarity	NPC11956
0.8046	Intermediate Similarity	NPC96362
0.8043	Intermediate Similarity	NPC50488
0.8043	Intermediate Similarity	NPC170633
0.8043	Intermediate Similarity	NPC474396
0.8041	Intermediate Similarity	NPC251680
0.8041	Intermediate Similarity	NPC474012
0.8041	Intermediate Similarity	NPC47024
0.8041	Intermediate Similarity	NPC476299
0.8023	Intermediate Similarity	NPC476949
0.8022	Intermediate Similarity	NPC245004
0.8022	Intermediate Similarity	NPC166857
0.8022	Intermediate Similarity	NPC471779
0.8021	Intermediate Similarity	NPC253826
0.8021	Intermediate Similarity	NPC189880
0.8021	Intermediate Similarity	NPC73911
0.802	Intermediate Similarity	NPC470024
0.802	Intermediate Similarity	NPC475263
0.802	Intermediate Similarity	NPC306265
0.8	Intermediate Similarity	NPC53565
0.8	Intermediate Similarity	NPC471786
0.8	Intermediate Similarity	NPC183012
0.8	Intermediate Similarity	NPC37603
0.8	Intermediate Similarity	NPC265588
0.798	Intermediate Similarity	NPC247957
0.798	Intermediate Similarity	NPC249187
0.798	Intermediate Similarity	NPC471938
0.798	Intermediate Similarity	NPC45897
0.7979	Intermediate Similarity	NPC472640
0.7979	Intermediate Similarity	NPC139692
0.7979	Intermediate Similarity	NPC472812
0.7979	Intermediate Similarity	NPC53555
0.7979	Intermediate Similarity	NPC7349
0.7979	Intermediate Similarity	NPC472641
0.7976	Intermediate Similarity	NPC306727
0.7959	Intermediate Similarity	NPC282524
0.7959	Intermediate Similarity	NPC472924
0.7959	Intermediate Similarity	NPC473160
0.7959	Intermediate Similarity	NPC115862
0.7959	Intermediate Similarity	NPC97435
0.7959	Intermediate Similarity	NPC96784
0.7959	Intermediate Similarity	NPC115899
0.7959	Intermediate Similarity	NPC471412
0.7959	Intermediate Similarity	NPC235920
0.7957	Intermediate Similarity	NPC310479
0.7957	Intermediate Similarity	NPC126369
0.7957	Intermediate Similarity	NPC182136
0.7957	Intermediate Similarity	NPC232202
0.7957	Intermediate Similarity	NPC472642
0.7957	Intermediate Similarity	NPC470589
0.7957	Intermediate Similarity	NPC221111
0.7957	Intermediate Similarity	NPC280149
0.7957	Intermediate Similarity	NPC111110
0.7955	Intermediate Similarity	NPC142163
0.7938	Intermediate Similarity	NPC114274
0.7938	Intermediate Similarity	NPC278386
0.7938	Intermediate Similarity	NPC247233
0.7938	Intermediate Similarity	NPC159763
0.7938	Intermediate Similarity	NPC124512
0.7938	Intermediate Similarity	NPC92275
0.7935	Intermediate Similarity	NPC48107
0.7931	Intermediate Similarity	NPC470429
0.7931	Intermediate Similarity	NPC242767
0.7921	Intermediate Similarity	NPC473586
0.7921	Intermediate Similarity	NPC109376
0.7917	Intermediate Similarity	NPC472941
0.7917	Intermediate Similarity	NPC476327
0.7917	Intermediate Similarity	NPC476318
0.7917	Intermediate Similarity	NPC242848
0.7917	Intermediate Similarity	NPC472995
0.7917	Intermediate Similarity	NPC116457

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 NPC314727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1518
0.2-0.3	3784
0.3-0.4	2350
0.4-0.5	893
0.5-0.6	210
0.6-0.7	223
0.7-0.8	11
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
0.8041	Intermediate Similarity	NPD7640	Approved
0.8041	Intermediate Similarity	NPD7639	Approved
0.7938	Intermediate Similarity	NPD7638	Approved
0.7938	Intermediate Similarity	NPD4225	Approved
0.7872	Intermediate Similarity	NPD7515	Phase 2
0.76	Intermediate Similarity	NPD5344	Discontinued
0.7526	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD7637	Suspended
0.7423	Intermediate Similarity	NPD5778	Approved
0.7423	Intermediate Similarity	NPD5779	Approved
0.7353	Intermediate Similarity	NPD7632	Discontinued
0.734	Intermediate Similarity	NPD3618	Phase 1
0.7333	Intermediate Similarity	NPD6929	Approved
0.7333	Intermediate Similarity	NPD7645	Phase 2
0.7327	Intermediate Similarity	NPD6648	Approved
0.732	Intermediate Similarity	NPD6079	Approved
0.73	Intermediate Similarity	NPD7902	Approved
0.7292	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD8264	Approved
0.7253	Intermediate Similarity	NPD6931	Approved
0.7253	Intermediate Similarity	NPD6930	Phase 2
0.7204	Intermediate Similarity	NPD6695	Phase 3
0.7184	Intermediate Similarity	NPD5211	Phase 2
0.717	Intermediate Similarity	NPD6881	Approved
0.717	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7128	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4786	Approved
0.7128	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6925	Approved
0.7111	Intermediate Similarity	NPD5776	Phase 2
0.7103	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3667	Approved
0.7083	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6942	Approved
0.7079	Intermediate Similarity	NPD7339	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7071	Intermediate Similarity	NPD6399	Phase 3
0.7065	Intermediate Similarity	NPD7332	Phase 2
0.7065	Intermediate Similarity	NPD7525	Registered
0.7065	Intermediate Similarity	NPD7514	Phase 3
0.7048	Intermediate Similarity	NPD5141	Approved
0.7037	Intermediate Similarity	NPD6883	Approved
0.7037	Intermediate Similarity	NPD7290	Approved
0.7037	Intermediate Similarity	NPD7102	Approved
0.7033	Intermediate Similarity	NPD7145	Approved
0.703	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5221	Approved
0.703	Intermediate Similarity	NPD5222	Approved
0.7009	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5286	Approved
0.699	Remote Similarity	NPD5285	Approved
0.699	Remote Similarity	NPD4696	Approved
0.6989	Remote Similarity	NPD6902	Approved
0.6972	Remote Similarity	NPD8130	Phase 1
0.6972	Remote Similarity	NPD6617	Approved
0.6972	Remote Similarity	NPD6649	Approved
0.6972	Remote Similarity	NPD6847	Approved
0.6972	Remote Similarity	NPD6869	Approved
0.6972	Remote Similarity	NPD6650	Approved
0.697	Remote Similarity	NPD6411	Approved
0.6961	Remote Similarity	NPD6084	Phase 2
0.6961	Remote Similarity	NPD6083	Phase 2
0.6961	Remote Similarity	NPD4755	Approved
0.6961	Remote Similarity	NPD5173	Approved
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6947	Remote Similarity	NPD3666	Approved
0.6944	Remote Similarity	NPD6373	Approved
0.6944	Remote Similarity	NPD6372	Approved
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6915	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8297	Approved
0.6909	Remote Similarity	NPD6882	Approved
0.6907	Remote Similarity	NPD7750	Discontinued
0.6907	Remote Similarity	NPD7524	Approved
0.6903	Remote Similarity	NPD7328	Approved
0.6903	Remote Similarity	NPD7327	Approved
0.69	Remote Similarity	NPD4202	Approved
0.6882	Remote Similarity	NPD4695	Discontinued
0.6881	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1696	Phase 3
0.6875	Remote Similarity	NPD6893	Approved
0.6875	Remote Similarity	NPD1694	Approved
0.6869	Remote Similarity	NPD7838	Discovery
0.6863	Remote Similarity	NPD4697	Phase 3
0.6857	Remote Similarity	NPD4633	Approved
0.6857	Remote Similarity	NPD5226	Approved
0.6857	Remote Similarity	NPD5225	Approved
0.6857	Remote Similarity	NPD5224	Approved
0.6852	Remote Similarity	NPD6011	Approved
0.6847	Remote Similarity	NPD4632	Approved
0.6842	Remote Similarity	NPD7516	Approved
0.6827	Remote Similarity	NPD4700	Approved
0.6809	Remote Similarity	NPD6898	Phase 1
0.6804	Remote Similarity	NPD7521	Approved
0.6804	Remote Similarity	NPD5330	Approved
0.6804	Remote Similarity	NPD7334	Approved
0.6804	Remote Similarity	NPD6684	Approved
0.6804	Remote Similarity	NPD7146	Approved
0.6804	Remote Similarity	NPD6409	Approved
0.6792	Remote Similarity	NPD5174	Approved
0.6792	Remote Similarity	NPD5175	Approved
0.6768	Remote Similarity	NPD6101	Approved
0.6768	Remote Similarity	NPD4753	Phase 2
0.6768	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5695	Phase 3
0.6762	Remote Similarity	NPD5223	Approved
0.6739	Remote Similarity	NPD6932	Approved
0.6735	Remote Similarity	NPD3573	Approved
0.6727	Remote Similarity	NPD4634	Approved
0.6724	Remote Similarity	NPD8379	Approved
0.6724	Remote Similarity	NPD8033	Approved
0.6724	Remote Similarity	NPD7503	Approved
0.6724	Remote Similarity	NPD8296	Approved
0.6724	Remote Similarity	NPD8378	Approved
0.6724	Remote Similarity	NPD8380	Approved
0.6724	Remote Similarity	NPD8335	Approved
0.6702	Remote Similarity	NPD4821	Approved
0.6702	Remote Similarity	NPD4819	Approved
0.6702	Remote Similarity	NPD4820	Approved
0.6702	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4822	Approved
0.6701	Remote Similarity	NPD5363	Approved
0.67	Remote Similarity	NPD6698	Approved
0.67	Remote Similarity	NPD46	Approved
0.67	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4268	Approved
0.6638	Remote Similarity	NPD8377	Approved
0.6638	Remote Similarity	NPD8294	Approved
0.6638	Remote Similarity	NPD6319	Approved
0.6634	Remote Similarity	NPD7087	Discontinued
0.6633	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4623	Approved
0.6633	Remote Similarity	NPD5279	Phase 3
0.6633	Remote Similarity	NPD4519	Discontinued
0.6607	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD6412	Phase 2
0.6606	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5210	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.66	Remote Similarity	NPD6051	Approved
0.6598	Remote Similarity	NPD3668	Phase 3
0.6596	Remote Similarity	NPD6683	Phase 2
0.6596	Remote Similarity	NPD4195	Approved
0.6593	Remote Similarity	NPD6926	Approved
0.6593	Remote Similarity	NPD6924	Approved
0.6579	Remote Similarity	NPD6868	Approved
0.6579	Remote Similarity	NPD6274	Approved
0.6571	Remote Similarity	NPD5696	Approved
0.6571	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5290	Discontinued
0.6555	Remote Similarity	NPD7492	Approved
0.6552	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD7100	Approved
0.6545	Remote Similarity	NPD4729	Approved
0.6545	Remote Similarity	NPD5128	Approved
0.6545	Remote Similarity	NPD4730	Approved
0.6526	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4768	Approved
0.6514	Remote Similarity	NPD4767	Approved
0.6509	Remote Similarity	NPD6404	Discontinued
0.65	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD7507	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6495	Remote Similarity	NPD7154	Phase 3
0.6495	Remote Similarity	NPD5331	Approved
0.6495	Remote Similarity	NPD5332	Approved
0.6495	Remote Similarity	NPD5362	Discontinued
0.6489	Remote Similarity	NPD6115	Approved
0.6489	Remote Similarity	NPD6697	Approved
0.6489	Remote Similarity	NPD6114	Approved
0.6489	Remote Similarity	NPD6118	Approved
0.6489	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4754	Approved
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD5281	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