NPASS Compound

Structure

NPC471553 OpenBabel07101718312D 21 22 0 0 1 0 0 0 0 0999 V2000 0.0000 -2.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4482 -0.0663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 -2.3913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 -0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6003 0.4288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 -0.4783 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.8479 -0.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6764 0.6764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1715 -1.1715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2476 -0.9239 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4288 1.6003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4191 -2.0954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4288 -1.6003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 0.9483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7718 -0.7427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 21 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 10 2 0 0 0 0 8 10 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 17 2 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	293.675
LogP:	1.547
LogD:	1.298
LogS:	-2.863
# Rotatable Bonds:	4
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	4.033
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.538
MDCK Permeability:	3.16091682179831e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.857
Plasma Protein Binding (PPB):	73.81884002685547%
Volume Distribution (VD):	0.456
Pgp-substrate:	16.109329223632812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.703
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.775

ADMET: Excretion

Clearance (CL):	1.912
Half-life (T1/2):	0.216

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.772
Rat Oral Acute Toxicity:	0.647
Maximum Recommended Daily Dose:	0.125
Skin Sensitization:	0.213
Carcinogencity:	0.619
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC471553

Natural Product ID:	NPC471553
*Common Name:**	5,6-Dihydroxy-2-Methoxy-5-(1-Phenylallyl)Cyclohex-2-Ene-1,4-Dione
IUPAC Name:	5,6-dihydroxy-2-methoxy-5-(1-phenylprop-2-enyl)cyclohex-2-ene-1,4-dione
Synonyms:
Standard InCHIKey:	WQCNPLOKEWOMRG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-3-11(10-7-5-4-6-8-10)16(20)13(17)9-12(21-2)14(18)15(16)19/h3-9,11,15,19-20H,1H2,2H3
SMILES:	COC1=CC(=O)C(C(C1=O)O)(O)C(c1ccccc1)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256508
PubChem CID:	24761039
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0001758] Dalbergiones

*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
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18154272]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22212722]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1830	Dalbergia sissoo	Species	Fabaceae	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	1
Others	1

Activity Type	# Activity
CELL-LINE	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	3190.0	nM	PMID[543905]
NPT27	Others	Unspecified		Activity	>	100.0	uM	PMID[543905]

☑ 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 NPC471553 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	224
0.1-0.2	853
0.2-0.3	2292
0.3-0.4	6838
0.4-0.5	12202
0.5-0.6	14644
0.6-0.7	5293
0.7-0.8	338
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8349	Intermediate Similarity	NPC145052
0.824	Intermediate Similarity	NPC81135
0.8235	Intermediate Similarity	NPC108532
0.8211	Intermediate Similarity	NPC65627
0.8174	Intermediate Similarity	NPC475282
0.8115	Intermediate Similarity	NPC105709
0.8016	Intermediate Similarity	NPC236405
0.7966	Intermediate Similarity	NPC292834
0.7913	Intermediate Similarity	NPC474307
0.7845	Intermediate Similarity	NPC25385
0.7845	Intermediate Similarity	NPC193640
0.7845	Intermediate Similarity	NPC475905
0.7815	Intermediate Similarity	NPC477250
0.7805	Intermediate Similarity	NPC318173
0.7798	Intermediate Similarity	NPC476484
0.7734	Intermediate Similarity	NPC294050
0.7734	Intermediate Similarity	NPC328997
0.7727	Intermediate Similarity	NPC144257
0.7724	Intermediate Similarity	NPC80605
0.7724	Intermediate Similarity	NPC222968
0.7724	Intermediate Similarity	NPC323440
0.7719	Intermediate Similarity	NPC112552
0.7706	Intermediate Similarity	NPC67585
0.7706	Intermediate Similarity	NPC110420
0.7706	Intermediate Similarity	NPC303967
0.7705	Intermediate Similarity	NPC471616
0.7699	Intermediate Similarity	NPC317280
0.7699	Intermediate Similarity	NPC329387
0.7664	Intermediate Similarity	NPC136649
0.7642	Intermediate Similarity	NPC28951
0.7642	Intermediate Similarity	NPC325646
0.7632	Intermediate Similarity	NPC476042
0.7615	Intermediate Similarity	NPC316553
0.7611	Intermediate Similarity	NPC103048
0.7594	Intermediate Similarity	NPC477680
0.7586	Intermediate Similarity	NPC274443
0.7565	Intermediate Similarity	NPC158623
0.7557	Intermediate Similarity	NPC469930
0.7542	Intermediate Similarity	NPC100767
0.7541	Intermediate Similarity	NPC326664
0.7541	Intermediate Similarity	NPC241851
0.754	Intermediate Similarity	NPC475827
0.754	Intermediate Similarity	NPC474223
0.7538	Intermediate Similarity	NPC146239
0.7537	Intermediate Similarity	NPC136994
0.7537	Intermediate Similarity	NPC88255
0.7522	Intermediate Similarity	NPC12695
0.7519	Intermediate Similarity	NPC317163
0.7517	Intermediate Similarity	NPC327225
0.75	Intermediate Similarity	NPC49272
0.75	Intermediate Similarity	NPC262819
0.75	Intermediate Similarity	NPC244427
0.75	Intermediate Similarity	NPC222390
0.7481	Intermediate Similarity	NPC478165
0.7481	Intermediate Similarity	NPC478162
0.748	Intermediate Similarity	NPC470764
0.7479	Intermediate Similarity	NPC20485
0.7479	Intermediate Similarity	NPC470391
0.7478	Intermediate Similarity	NPC54647
0.7478	Intermediate Similarity	NPC474308
0.7477	Intermediate Similarity	NPC187725
0.7477	Intermediate Similarity	NPC141607
0.7465	Intermediate Similarity	NPC136878
0.746	Intermediate Similarity	NPC204784
0.7459	Intermediate Similarity	NPC143768
0.7458	Intermediate Similarity	NPC172483
0.7456	Intermediate Similarity	NPC289201
0.7456	Intermediate Similarity	NPC156021
0.7442	Intermediate Similarity	NPC471466
0.7442	Intermediate Similarity	NPC318067
0.7442	Intermediate Similarity	NPC325740
0.7442	Intermediate Similarity	NPC328107
0.7438	Intermediate Similarity	NPC137315
0.7434	Intermediate Similarity	NPC473347
0.7426	Intermediate Similarity	NPC309056
0.7419	Intermediate Similarity	NPC62138
0.7417	Intermediate Similarity	NPC192577
0.7402	Intermediate Similarity	NPC475804
0.7402	Intermediate Similarity	NPC474222
0.7391	Intermediate Similarity	NPC476120
0.7391	Intermediate Similarity	NPC173980
0.7388	Intermediate Similarity	NPC108553
0.7385	Intermediate Similarity	NPC478108
0.7377	Intermediate Similarity	NPC218855
0.7373	Intermediate Similarity	NPC19136
0.7364	Intermediate Similarity	NPC139171
0.7364	Intermediate Similarity	NPC474159
0.7364	Intermediate Similarity	NPC477704
0.7364	Intermediate Similarity	NPC474254
0.7364	Intermediate Similarity	NPC477693
0.7361	Intermediate Similarity	NPC101043
0.7361	Intermediate Similarity	NPC306799
0.7353	Intermediate Similarity	NPC212207
0.7348	Intermediate Similarity	NPC477370
0.7348	Intermediate Similarity	NPC472707
0.7345	Intermediate Similarity	NPC34243
0.7339	Intermediate Similarity	NPC217111
0.7338	Intermediate Similarity	NPC477408
0.7333	Intermediate Similarity	NPC203732
0.7333	Intermediate Similarity	NPC470007
0.7328	Intermediate Similarity	NPC477366
0.7328	Intermediate Similarity	NPC477363
0.7324	Intermediate Similarity	NPC29932
0.7323	Intermediate Similarity	NPC476645
0.7321	Intermediate Similarity	NPC317645
0.7317	Intermediate Similarity	NPC477246
0.7317	Intermediate Similarity	NPC477245
0.7317	Intermediate Similarity	NPC477476
0.7317	Intermediate Similarity	NPC477475
0.7313	Intermediate Similarity	NPC17567
0.7313	Intermediate Similarity	NPC319995
0.7313	Intermediate Similarity	NPC289415
0.7304	Intermediate Similarity	NPC278228
0.7304	Intermediate Similarity	NPC477767
0.7302	Intermediate Similarity	NPC61651
0.7297	Intermediate Similarity	NPC231591
0.7295	Intermediate Similarity	NPC477247
0.7293	Intermediate Similarity	NPC37968
0.7288	Intermediate Similarity	NPC247976
0.7281	Intermediate Similarity	NPC206764
0.728	Intermediate Similarity	NPC23402
0.7273	Intermediate Similarity	NPC51037
0.7273	Intermediate Similarity	NPC40178
0.7273	Intermediate Similarity	NPC477365
0.726	Intermediate Similarity	NPC219419
0.7258	Intermediate Similarity	NPC130591
0.7258	Intermediate Similarity	NPC234637
0.7254	Intermediate Similarity	NPC301946
0.7254	Intermediate Similarity	NPC277053
0.7252	Intermediate Similarity	NPC244454
0.7252	Intermediate Similarity	NPC231767
0.725	Intermediate Similarity	NPC474111
0.725	Intermediate Similarity	NPC329705
0.7244	Intermediate Similarity	NPC104514
0.7241	Intermediate Similarity	NPC471103
0.7241	Intermediate Similarity	NPC271475
0.7239	Intermediate Similarity	NPC471832
0.7236	Intermediate Similarity	NPC471189
0.7227	Intermediate Similarity	NPC329282
0.7227	Intermediate Similarity	NPC249067
0.7226	Intermediate Similarity	NPC477210
0.7226	Intermediate Similarity	NPC23894
0.7222	Intermediate Similarity	NPC469843
0.7214	Intermediate Similarity	NPC474303
0.7214	Intermediate Similarity	NPC475413
0.7211	Intermediate Similarity	NPC114357
0.7211	Intermediate Similarity	NPC155329
0.7211	Intermediate Similarity	NPC259144
0.7209	Intermediate Similarity	NPC476234
0.7206	Intermediate Similarity	NPC15850
0.7203	Intermediate Similarity	NPC477737
0.72	Intermediate Similarity	NPC474408
0.72	Intermediate Similarity	NPC215419
0.72	Intermediate Similarity	NPC469509
0.72	Intermediate Similarity	NPC285350
0.7197	Intermediate Similarity	NPC476033
0.7197	Intermediate Similarity	NPC79608
0.719	Intermediate Similarity	NPC47536
0.7185	Intermediate Similarity	NPC60825
0.7185	Intermediate Similarity	NPC291419
0.7185	Intermediate Similarity	NPC471334
0.7183	Intermediate Similarity	NPC80895
0.7183	Intermediate Similarity	NPC471912
0.7177	Intermediate Similarity	NPC469547
0.7177	Intermediate Similarity	NPC471481
0.7177	Intermediate Similarity	NPC470253
0.7176	Intermediate Similarity	NPC477362
0.7176	Intermediate Similarity	NPC140118
0.7176	Intermediate Similarity	NPC138798
0.7176	Intermediate Similarity	NPC12881
0.7172	Intermediate Similarity	NPC198455
0.7172	Intermediate Similarity	NPC161239
0.7172	Intermediate Similarity	NPC165260
0.7167	Intermediate Similarity	NPC134120
0.7167	Intermediate Similarity	NPC471186
0.7164	Intermediate Similarity	NPC237225
0.7154	Intermediate Similarity	NPC265513
0.7154	Intermediate Similarity	NPC291799
0.7153	Intermediate Similarity	NPC205389
0.7153	Intermediate Similarity	NPC477368
0.7143	Intermediate Similarity	NPC11588
0.7143	Intermediate Similarity	NPC474250
0.7143	Intermediate Similarity	NPC134685
0.7143	Intermediate Similarity	NPC329556
0.7143	Intermediate Similarity	NPC248265
0.7143	Intermediate Similarity	NPC260886
0.7143	Intermediate Similarity	NPC477357
0.7143	Intermediate Similarity	NPC229545
0.7133	Intermediate Similarity	NPC127857
0.7133	Intermediate Similarity	NPC143898
0.7132	Intermediate Similarity	NPC80599
0.7132	Intermediate Similarity	NPC209851
0.7123	Intermediate Similarity	NPC112816
0.7123	Intermediate Similarity	NPC51602
0.7122	Intermediate Similarity	NPC475549
0.7121	Intermediate Similarity	NPC295664
0.7121	Intermediate Similarity	NPC474803
0.7121	Intermediate Similarity	NPC246166
0.7121	Intermediate Similarity	NPC477369
0.712	Intermediate Similarity	NPC67377

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 NPC471553 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	740
0.2-0.3	1485
0.3-0.4	2955
0.4-0.5	2297
0.5-0.6	1210
0.6-0.7	255
0.7-0.8	13
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
0.7881	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2067	Discontinued
0.7328	Intermediate Similarity	NPD2066	Phase 3
0.7227	Intermediate Similarity	NPD1237	Approved
0.72	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2629	Approved
0.7143	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1929	Approved
0.7143	Intermediate Similarity	NPD1930	Approved
0.7143	Intermediate Similarity	NPD6647	Phase 2
0.7025	Intermediate Similarity	NPD5048	Discontinued
0.6967	Remote Similarity	NPD6685	Approved
0.6949	Remote Similarity	NPD9495	Approved
0.6897	Remote Similarity	NPD7236	Approved
0.6889	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5765	Approved
0.685	Remote Similarity	NPD2652	Approved
0.685	Remote Similarity	NPD2650	Approved
0.6838	Remote Similarity	NPD1693	Approved
0.6818	Remote Similarity	NPD4879	Approved
0.6803	Remote Similarity	NPD5909	Discontinued
0.6783	Remote Similarity	NPD1090	Approved
0.6783	Remote Similarity	NPD1089	Approved
0.6783	Remote Similarity	NPD1086	Approved
0.6777	Remote Similarity	NPD1932	Approved
0.6763	Remote Similarity	NPD7961	Discontinued
0.6744	Remote Similarity	NPD4198	Discontinued
0.6742	Remote Similarity	NPD5305	Approved
0.6742	Remote Similarity	NPD5306	Approved
0.6721	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2329	Discontinued
0.6712	Remote Similarity	NPD6190	Approved
0.6696	Remote Similarity	NPD800	Approved
0.6693	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD7631	Approved
0.6667	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD1088	Approved
0.6643	Remote Similarity	NPD6233	Phase 2
0.6642	Remote Similarity	NPD2610	Approved
0.6642	Remote Similarity	NPD4217	Approved
0.6642	Remote Similarity	NPD4216	Approved
0.6642	Remote Similarity	NPD3131	Approved
0.6642	Remote Similarity	NPD4215	Approved
0.6642	Remote Similarity	NPD2611	Approved
0.6642	Remote Similarity	NPD2612	Approved
0.6642	Remote Similarity	NPD4807	Approved
0.6642	Remote Similarity	NPD4218	Approved
0.6642	Remote Similarity	NPD2609	Approved
0.6642	Remote Similarity	NPD4806	Approved
0.6642	Remote Similarity	NPD2608	Approved
0.6642	Remote Similarity	NPD3132	Approved
0.6641	Remote Similarity	NPD6858	Approved
0.6641	Remote Similarity	NPD7094	Approved
0.6639	Remote Similarity	NPD1989	Approved
0.6638	Remote Similarity	NPD3672	Approved
0.6638	Remote Similarity	NPD3673	Approved
0.6617	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3317	Approved
0.6612	Remote Similarity	NPD7798	Approved
0.6589	Remote Similarity	NPD6010	Discontinued
0.6587	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2182	Approved
0.6581	Remote Similarity	NPD7609	Phase 3
0.6567	Remote Similarity	NPD4135	Approved
0.6567	Remote Similarity	NPD4136	Approved
0.6567	Remote Similarity	NPD4106	Approved
0.6562	Remote Similarity	NPD6912	Phase 3
0.6558	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3300	Phase 2
0.6552	Remote Similarity	NPD5346	Phase 2
0.6552	Remote Similarity	NPD5347	Phase 2
0.6547	Remote Similarity	NPD2613	Approved
0.6535	Remote Similarity	NPD1317	Discontinued
0.6522	Remote Similarity	NPD2798	Approved
0.6522	Remote Similarity	NPD3751	Discontinued
0.6522	Remote Similarity	NPD6085	Phase 2
0.6522	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1087	Approved
0.651	Remote Similarity	NPD6799	Approved
0.6484	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6599	Discontinued
0.6471	Remote Similarity	NPD4380	Phase 2
0.6467	Remote Similarity	NPD8434	Phase 2
0.6466	Remote Similarity	NPD7009	Phase 2
0.6463	Remote Similarity	NPD8368	Discontinued
0.646	Remote Similarity	NPD9491	Approved
0.6454	Remote Similarity	NPD6798	Discontinued
0.6446	Remote Similarity	NPD1564	Approved
0.6446	Remote Similarity	NPD1565	Approved
0.6446	Remote Similarity	NPD1566	Phase 3
0.6444	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD1239	Approved
0.6439	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7075	Discontinued
0.6429	Remote Similarity	NPD226	Approved
0.6423	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD2575	Approved
0.6419	Remote Similarity	NPD4628	Phase 3
0.6418	Remote Similarity	NPD4102	Approved
0.6418	Remote Similarity	NPD4105	Approved
0.6417	Remote Similarity	NPD688	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5402	Approved
0.6408	Remote Similarity	NPD2571	Approved
0.6408	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3089	Approved
0.6408	Remote Similarity	NPD2573	Approved
0.6408	Remote Similarity	NPD3088	Approved
0.6408	Remote Similarity	NPD2574	Discontinued
0.6408	Remote Similarity	NPD4745	Approved
0.6408	Remote Similarity	NPD3615	Approved
0.6408	Remote Similarity	NPD2566	Approved
0.6408	Remote Similarity	NPD3087	Approved
0.6408	Remote Similarity	NPD2570	Approved
0.6408	Remote Similarity	NPD3614	Approved
0.6408	Remote Similarity	NPD3090	Approved
0.6408	Remote Similarity	NPD3616	Approved
0.6408	Remote Similarity	NPD4746	Phase 3
0.6403	Remote Similarity	NPD5647	Approved
0.64	Remote Similarity	NPD164	Approved
0.6391	Remote Similarity	NPD7610	Discontinued
0.6387	Remote Similarity	NPD6801	Discontinued
0.6382	Remote Similarity	NPD5403	Approved
0.6379	Remote Similarity	NPD4793	Discontinued
0.6379	Remote Similarity	NPD650	Approved
0.637	Remote Similarity	NPD2935	Discontinued
0.6369	Remote Similarity	NPD7057	Phase 3
0.6369	Remote Similarity	NPD7058	Phase 2
0.6358	Remote Similarity	NPD5401	Approved
0.6358	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5204	Approved
0.6357	Remote Similarity	NPD3663	Approved
0.6357	Remote Similarity	NPD3662	Phase 3
0.6357	Remote Similarity	NPD3664	Approved
0.6357	Remote Similarity	NPD3661	Approved
0.635	Remote Similarity	NPD4878	Approved
0.6347	Remote Similarity	NPD8407	Phase 2
0.6338	Remote Similarity	NPD3268	Approved
0.6336	Remote Similarity	NPD1241	Discontinued
0.6319	Remote Similarity	NPD4685	Phase 3
0.6319	Remote Similarity	NPD4684	Phase 3
0.6319	Remote Similarity	NPD4686	Approved
0.6319	Remote Similarity	NPD7799	Discontinued
0.6312	Remote Similarity	NPD4620	Approved
0.6312	Remote Similarity	NPD5201	Approved
0.6312	Remote Similarity	NPD5203	Approved
0.6312	Remote Similarity	NPD4617	Approved
0.6311	Remote Similarity	NPD3495	Discontinued
0.6309	Remote Similarity	NPD8166	Discontinued
0.6309	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD969	Suspended
0.6304	Remote Similarity	NPD5157	Phase 1
0.6304	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5159	Phase 2
0.6301	Remote Similarity	NPD1510	Phase 2
0.6301	Remote Similarity	NPD2799	Discontinued
0.6301	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4062	Phase 3
0.6288	Remote Similarity	NPD5951	Approved
0.6284	Remote Similarity	NPD2424	Discontinued
0.6273	Remote Similarity	NPD3787	Discontinued
0.6268	Remote Similarity	NPD4738	Phase 2
0.6268	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD3882	Suspended
0.6259	Remote Similarity	NPD1876	Approved
0.6259	Remote Similarity	NPD2796	Approved
0.625	Remote Similarity	NPD5120	Approved
0.625	Remote Similarity	NPD943	Approved
0.625	Remote Similarity	NPD1240	Approved
0.625	Remote Similarity	NPD5121	Approved
0.625	Remote Similarity	NPD2932	Approved
0.625	Remote Similarity	NPD2345	Approved
0.625	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5119	Approved
0.6242	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD7084	Phase 3
0.6232	Remote Similarity	NPD3972	Approved
0.6232	Remote Similarity	NPD6637	Approved
0.6226	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD2313	Discontinued
0.6222	Remote Similarity	NPD7741	Discontinued
0.6221	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1470	Approved
0.6214	Remote Similarity	NPD2625	Approved
0.6214	Remote Similarity	NPD2797	Approved
0.6214	Remote Similarity	NPD2627	Approved
0.6214	Remote Similarity	NPD2160	Approved
0.6214	Remote Similarity	NPD2628	Approved
0.6214	Remote Similarity	NPD2159	Approved
0.6214	Remote Similarity	NPD2626	Approved
0.6203	Remote Similarity	NPD3817	Phase 2
0.6199	Remote Similarity	NPD8435	Approved
0.6198	Remote Similarity	NPD1563	Approved
0.6198	Remote Similarity	NPD5282	Discontinued
0.6197	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6166	Phase 2

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