NPASS Compound

Structure

CID172673 OpenBabel06191715542D 22 23 0 0 0 0 0 0 0 0999 V2000 7.7942 -2.5000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 6.9282 -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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 7.7942 0.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 12 14 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	310.971
LogP:	2.771
LogD:	3.24
LogS:	-3.276
# Rotatable Bonds:	5
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.416
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.852
MDCK Permeability:	1.6085064999060705e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.202

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	98.97240447998047%
Volume Distribution (VD):	0.616
Pgp-substrate:	1.523484230041504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.917
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.578
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.613
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.564
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	14.31
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.291
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.819
Skin Sensitization:	0.949
Carcinogencity:	0.303
Eye Corrosion:	0.013
Eye Irritation:	0.932
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC172673

Natural Product ID:	NPC172673
*Common Name:**	Griffithane D
IUPAC Name:	2-[3-(4-hydroxy-3-methoxyphenyl)propyl]-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	Griffithane D
Standard InCHIKey:	QMDYKPDQQKWJLM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O5/c1-21-16-8-11(6-7-13(16)18)4-3-5-12-9-15(20)17(22-2)10-14(12)19/h6-10,18H,3-5H2,1-2H3
SMILES:	COC1=CC(=O)C(=CC1=O)CCCc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1834919
PubChem CID:	56597215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	n.a.	stem	n.a.	PMID[21919533]
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23795891]
NPO12425	Combretum griffithii	Species	Combretaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.42	ug.mL-1	PMID[545078]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	1.08	ug.mL-1	PMID[545078]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6.75	ug.mL-1	PMID[545078]

☑ 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 NPC172673 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	312
0.1-0.2	1431
0.2-0.3	4063
0.3-0.4	10023
0.4-0.5	8137
0.5-0.6	4260
0.6-0.7	9304
0.7-0.8	4752
0.8-0.85	274
0.85-0.9	110
0.9-0.95	29
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.984	High Similarity	NPC239302
0.9444	High Similarity	NPC304622
0.944	High Similarity	NPC5018
0.944	High Similarity	NPC123228
0.944	High Similarity	NPC276466
0.944	High Similarity	NPC151167
0.944	High Similarity	NPC123722
0.9431	High Similarity	NPC257976
0.9431	High Similarity	NPC242372
0.9431	High Similarity	NPC4181
0.9431	High Similarity	NPC164778
0.936	High Similarity	NPC179777
0.936	High Similarity	NPC303680
0.936	High Similarity	NPC84076
0.936	High Similarity	NPC90128
0.9355	High Similarity	NPC312404
0.9355	High Similarity	NPC273686
0.935	High Similarity	NPC114298
0.9318	High Similarity	NPC322021
0.9302	High Similarity	NPC327410
0.928	High Similarity	NPC53305
0.928	High Similarity	NPC257589
0.9274	High Similarity	NPC163083
0.9268	High Similarity	NPC201777
0.9206	High Similarity	NPC92207
0.9206	High Similarity	NPC127937
0.9194	High Similarity	NPC286573
0.9187	High Similarity	NPC158949
0.9098	High Similarity	NPC284409
0.9062	High Similarity	NPC226661
0.9055	High Similarity	NPC276014
0.9024	High Similarity	NPC299406
0.8984	High Similarity	NPC12022
0.8984	High Similarity	NPC293641
0.8984	High Similarity	NPC20287
0.8984	High Similarity	NPC20404
0.8968	High Similarity	NPC106659
0.8968	High Similarity	NPC18984
0.8968	High Similarity	NPC229084
0.8968	High Similarity	NPC160900
0.8923	High Similarity	NPC311419
0.8923	High Similarity	NPC123196
0.8923	High Similarity	NPC244246
0.8923	High Similarity	NPC319282
0.8923	High Similarity	NPC215941
0.8923	High Similarity	NPC137427
0.8923	High Similarity	NPC66905
0.8923	High Similarity	NPC275724
0.8923	High Similarity	NPC65935
0.8915	High Similarity	NPC278308
0.8889	High Similarity	NPC288452
0.8889	High Similarity	NPC289690
0.888	High Similarity	NPC269843
0.888	High Similarity	NPC14007
0.888	High Similarity	NPC60962
0.888	High Similarity	NPC109083
0.888	High Similarity	NPC224814
0.888	High Similarity	NPC189844
0.8837	High Similarity	NPC16651
0.8837	High Similarity	NPC32163
0.8828	High Similarity	NPC280767
0.8828	High Similarity	NPC3221
0.881	High Similarity	NPC194416
0.881	High Similarity	NPC177291
0.8806	High Similarity	NPC90431
0.8797	High Similarity	NPC471110
0.8788	High Similarity	NPC153453
0.8769	High Similarity	NPC110313
0.8759	High Similarity	NPC472410
0.875	High Similarity	NPC474784
0.8731	High Similarity	NPC139519
0.8731	High Similarity	NPC204592
0.8722	High Similarity	NPC475468
0.8705	High Similarity	NPC258671
0.8705	High Similarity	NPC53884
0.8686	High Similarity	NPC78987
0.8686	High Similarity	NPC82336
0.8672	High Similarity	NPC244876
0.8652	High Similarity	NPC98009
0.8647	High Similarity	NPC50763
0.864	High Similarity	NPC470626
0.8636	High Similarity	NPC142985
0.8636	High Similarity	NPC477705
0.8636	High Similarity	NPC477694
0.8636	High Similarity	NPC195292
0.8633	High Similarity	NPC224884
0.8633	High Similarity	NPC209085
0.8633	High Similarity	NPC304956
0.8629	High Similarity	NPC268317
0.8615	High Similarity	NPC213552
0.8615	High Similarity	NPC120225
0.8605	High Similarity	NPC60517
0.8605	High Similarity	NPC20443
0.8605	High Similarity	NPC146886
0.8601	High Similarity	NPC295977
0.8601	High Similarity	NPC178048
0.8601	High Similarity	NPC58310
0.8593	High Similarity	NPC152209
0.8582	High Similarity	NPC143892
0.8582	High Similarity	NPC299090
0.8582	High Similarity	NPC221383
0.8582	High Similarity	NPC283081
0.8571	High Similarity	NPC477706
0.8571	High Similarity	NPC469480
0.8561	High Similarity	NPC192597
0.8561	High Similarity	NPC176030
0.8561	High Similarity	NPC229218
0.8561	High Similarity	NPC169214
0.8561	High Similarity	NPC241354
0.8561	High Similarity	NPC141817
0.856	High Similarity	NPC293619
0.856	High Similarity	NPC280001
0.8542	High Similarity	NPC306011
0.8542	High Similarity	NPC472838
0.854	High Similarity	NPC325625
0.8538	High Similarity	NPC289459
0.8521	High Similarity	NPC58373
0.8519	High Similarity	NPC68779
0.8519	High Similarity	NPC5310
0.8519	High Similarity	NPC300776
0.8519	High Similarity	NPC4982
0.8519	High Similarity	NPC176814
0.8504	High Similarity	NPC95614
0.8504	High Similarity	NPC56214
0.8504	High Similarity	NPC242885
0.8504	High Similarity	NPC232316
0.8504	High Similarity	NPC117780
0.8504	High Similarity	NPC227217
0.8504	High Similarity	NPC165133
0.85	High Similarity	NPC160378
0.85	High Similarity	NPC46880
0.85	High Similarity	NPC239608
0.85	High Similarity	NPC16353
0.85	High Similarity	NPC46161
0.8492	Intermediate Similarity	NPC272471
0.8492	Intermediate Similarity	NPC107588
0.8492	Intermediate Similarity	NPC137537
0.8492	Intermediate Similarity	NPC205502
0.8492	Intermediate Similarity	NPC164706
0.8492	Intermediate Similarity	NPC70744
0.8489	Intermediate Similarity	NPC476840
0.8489	Intermediate Similarity	NPC476842
0.8485	Intermediate Similarity	NPC478215
0.8483	Intermediate Similarity	NPC327225
0.848	Intermediate Similarity	NPC299252
0.848	Intermediate Similarity	NPC19290
0.848	Intermediate Similarity	NPC28951
0.848	Intermediate Similarity	NPC61062
0.848	Intermediate Similarity	NPC325646
0.848	Intermediate Similarity	NPC277394
0.8472	Intermediate Similarity	NPC475718
0.8462	Intermediate Similarity	NPC246704
0.8456	Intermediate Similarity	NPC113295
0.8444	Intermediate Similarity	NPC155209
0.8444	Intermediate Similarity	NPC168799
0.844	Intermediate Similarity	NPC207732
0.8438	Intermediate Similarity	NPC204466
0.8438	Intermediate Similarity	NPC207613
0.8433	Intermediate Similarity	NPC198388
0.8425	Intermediate Similarity	NPC310338
0.8425	Intermediate Similarity	NPC24474
0.8425	Intermediate Similarity	NPC311595
0.8425	Intermediate Similarity	NPC281298
0.8421	Intermediate Similarity	NPC83062
0.8417	Intermediate Similarity	NPC28398
0.8413	Intermediate Similarity	NPC164386
0.8413	Intermediate Similarity	NPC185738
0.8413	Intermediate Similarity	NPC39793
0.8409	Intermediate Similarity	NPC203719
0.8409	Intermediate Similarity	NPC281020
0.8409	Intermediate Similarity	NPC117237
0.8397	Intermediate Similarity	NPC87113
0.8385	Intermediate Similarity	NPC474691
0.838	Intermediate Similarity	NPC472560
0.838	Intermediate Similarity	NPC157133
0.8374	Intermediate Similarity	NPC257124
0.8374	Intermediate Similarity	NPC156840
0.8374	Intermediate Similarity	NPC8547
0.8374	Intermediate Similarity	NPC173746
0.8372	Intermediate Similarity	NPC160380
0.8372	Intermediate Similarity	NPC324571
0.8372	Intermediate Similarity	NPC54872
0.8372	Intermediate Similarity	NPC70752
0.8372	Intermediate Similarity	NPC343720
0.8372	Intermediate Similarity	NPC184651
0.8372	Intermediate Similarity	NPC113865
0.8372	Intermediate Similarity	NPC38996
0.8372	Intermediate Similarity	NPC473853
0.8372	Intermediate Similarity	NPC262156
0.8372	Intermediate Similarity	NPC312675
0.8372	Intermediate Similarity	NPC470212
0.837	Intermediate Similarity	NPC25581
0.837	Intermediate Similarity	NPC61
0.837	Intermediate Similarity	NPC5419
0.837	Intermediate Similarity	NPC111888
0.837	Intermediate Similarity	NPC18074
0.8369	Intermediate Similarity	NPC50954
0.8359	Intermediate Similarity	NPC202474
0.8359	Intermediate Similarity	NPC2058
0.8357	Intermediate Similarity	NPC253481

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 NPC172673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	940
0.2-0.3	1524
0.3-0.4	2545
0.4-0.5	2001
0.5-0.6	1092
0.6-0.7	653
0.7-0.8	104
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8968	High Similarity	NPD4379	Clinical (unspecified phase)
0.8413	Intermediate Similarity	NPD5536	Phase 2
0.8409	Intermediate Similarity	NPD9494	Approved
0.8374	Intermediate Similarity	NPD228	Approved
0.8067	Intermediate Similarity	NPD3882	Suspended
0.7953	Intermediate Similarity	NPD5283	Phase 1
0.7883	Intermediate Similarity	NPD3027	Phase 3
0.7847	Intermediate Similarity	NPD8166	Discontinued
0.7826	Intermediate Similarity	NPD6798	Discontinued
0.7812	Intermediate Similarity	NPD1241	Discontinued
0.7808	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6355	Discontinued
0.7754	Intermediate Similarity	NPD7095	Approved
0.7748	Intermediate Similarity	NPD1934	Approved
0.7714	Intermediate Similarity	NPD4060	Phase 1
0.7697	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7671	Intermediate Similarity	NPD6190	Approved
0.7643	Intermediate Similarity	NPD6233	Phase 2
0.7643	Intermediate Similarity	NPD4062	Phase 3
0.7638	Intermediate Similarity	NPD3022	Approved
0.7638	Intermediate Similarity	NPD3021	Approved
0.7616	Intermediate Similarity	NPD7028	Phase 2
0.7603	Intermediate Similarity	NPD4110	Phase 3
0.7603	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6166	Phase 2
0.7595	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1651	Approved
0.7584	Intermediate Similarity	NPD1512	Approved
0.7582	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD447	Suspended
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD3972	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7465	Intermediate Similarity	NPD3620	Phase 2
0.7465	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1511	Approved
0.7432	Intermediate Similarity	NPD2354	Approved
0.7422	Intermediate Similarity	NPD2684	Approved
0.7417	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD230	Phase 1
0.7407	Intermediate Similarity	NPD4626	Approved
0.7394	Intermediate Similarity	NPD2674	Phase 3
0.7391	Intermediate Similarity	NPD1283	Approved
0.7391	Intermediate Similarity	NPD1876	Approved
0.7372	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3847	Discontinued
0.7348	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4534	Discontinued
0.7344	Intermediate Similarity	NPD1358	Approved
0.7343	Intermediate Similarity	NPD1240	Approved
0.7343	Intermediate Similarity	NPD943	Approved
0.7333	Intermediate Similarity	NPD1357	Approved
0.7333	Intermediate Similarity	NPD6799	Approved
0.7328	Intermediate Similarity	NPD7843	Approved
0.7325	Intermediate Similarity	NPD7075	Discontinued
0.732	Intermediate Similarity	NPD3455	Phase 2
0.732	Intermediate Similarity	NPD824	Approved
0.7305	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7157	Approved
0.7286	Intermediate Similarity	NPD2798	Approved
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3818	Discontinued
0.7279	Intermediate Similarity	NPD2932	Approved
0.726	Intermediate Similarity	NPD2799	Discontinued
0.726	Intermediate Similarity	NPD1510	Phase 2
0.7256	Intermediate Similarity	NPD6797	Phase 2
0.7246	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1607	Approved
0.7237	Intermediate Similarity	NPD5049	Phase 3
0.7234	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5958	Discontinued
0.7222	Intermediate Similarity	NPD1613	Approved
0.7222	Intermediate Similarity	NPD826	Approved
0.7222	Intermediate Similarity	NPD825	Approved
0.7222	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4357	Discontinued
0.7214	Intermediate Similarity	NPD2797	Approved
0.7212	Intermediate Similarity	NPD7251	Discontinued
0.7208	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3268	Approved
0.7203	Intermediate Similarity	NPD3144	Approved
0.7203	Intermediate Similarity	NPD3145	Approved
0.72	Intermediate Similarity	NPD3887	Approved
0.7195	Intermediate Similarity	NPD7074	Phase 3
0.7194	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1535	Discovery
0.7174	Intermediate Similarity	NPD1281	Approved
0.7171	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3146	Approved
0.717	Intermediate Similarity	NPD6234	Discontinued
0.7169	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7808	Phase 3
0.7164	Intermediate Similarity	NPD6671	Approved
0.7163	Intermediate Similarity	NPD258	Approved
0.7163	Intermediate Similarity	NPD257	Approved
0.7162	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2353	Approved
0.7162	Intermediate Similarity	NPD2344	Approved
0.7162	Intermediate Similarity	NPD7266	Discontinued
0.7161	Intermediate Similarity	NPD4380	Phase 2
0.7161	Intermediate Similarity	NPD6599	Discontinued
0.7154	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD3019	Approved
0.7152	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7054	Approved
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3750	Approved
0.7132	Intermediate Similarity	NPD9545	Approved
0.7132	Intermediate Similarity	NPD3134	Approved
0.7132	Intermediate Similarity	NPD1894	Discontinued
0.7122	Intermediate Similarity	NPD1608	Approved
0.7122	Intermediate Similarity	NPD1481	Phase 2
0.7117	Intermediate Similarity	NPD7473	Discontinued
0.7115	Intermediate Similarity	NPD6873	Phase 2
0.7114	Intermediate Similarity	NPD2424	Discontinued
0.7103	Intermediate Similarity	NPD1558	Phase 1
0.7101	Intermediate Similarity	NPD3496	Discontinued
0.7099	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7458	Discontinued
0.7092	Intermediate Similarity	NPD987	Approved
0.7091	Intermediate Similarity	NPD7472	Approved
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.708	Intermediate Similarity	NPD5691	Approved
0.7071	Intermediate Similarity	NPD2982	Phase 2
0.7071	Intermediate Similarity	NPD2983	Phase 2
0.707	Intermediate Similarity	NPD6801	Discontinued
0.707	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD919	Approved
0.7055	Intermediate Similarity	NPD1933	Approved
0.7055	Intermediate Similarity	NPD4340	Discontinued
0.705	Intermediate Similarity	NPD3705	Approved
0.7042	Intermediate Similarity	NPD5647	Approved
0.7034	Intermediate Similarity	NPD259	Phase 1
0.7032	Intermediate Similarity	NPD1653	Approved
0.7025	Intermediate Similarity	NPD1465	Phase 2
0.702	Intermediate Similarity	NPD7003	Approved
0.7018	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6653	Approved
0.7006	Intermediate Similarity	NPD5089	Approved
0.7006	Intermediate Similarity	NPD5090	Approved
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD1549	Phase 2
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9269	Phase 2
0.7	Intermediate Similarity	NPD2981	Phase 2
0.6994	Remote Similarity	NPD3926	Phase 2
0.6993	Remote Similarity	NPD3018	Phase 2
0.6986	Remote Similarity	NPD2979	Phase 3
0.6985	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9493	Approved
0.6981	Remote Similarity	NPD5977	Approved
0.6981	Remote Similarity	NPD5978	Approved
0.6981	Remote Similarity	NPD5402	Approved
0.698	Remote Similarity	NPD2438	Suspended
0.698	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2821	Approved
0.6975	Remote Similarity	NPD1247	Approved
0.6974	Remote Similarity	NPD2309	Approved
0.6972	Remote Similarity	NPD1203	Approved
0.6968	Remote Similarity	NPD5403	Approved
0.6966	Remote Similarity	NPD2313	Discontinued
0.6966	Remote Similarity	NPD3764	Approved
0.6966	Remote Similarity	NPD5109	Approved
0.6966	Remote Similarity	NPD5110	Phase 2
0.6966	Remote Similarity	NPD5111	Phase 2
0.6966	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2859	Approved
0.696	Remote Similarity	NPD2860	Approved
0.6954	Remote Similarity	NPD3060	Approved
0.6951	Remote Similarity	NPD2898	Approved
0.6944	Remote Similarity	NPD2614	Approved
0.694	Remote Similarity	NPD5535	Approved
0.6939	Remote Similarity	NPD555	Phase 2
0.6937	Remote Similarity	NPD4966	Approved
0.6937	Remote Similarity	NPD4967	Phase 2
0.6937	Remote Similarity	NPD4965	Approved
0.6933	Remote Similarity	NPD2346	Discontinued
0.6933	Remote Similarity	NPD5763	Approved
0.6933	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5762	Approved
0.6929	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3020	Approved
0.6928	Remote Similarity	NPD5844	Phase 1
0.6923	Remote Similarity	NPD6584	Phase 3
0.6918	Remote Similarity	NPD8032	Phase 2
0.6918	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5494	Approved
0.6913	Remote Similarity	NPD4308	Phase 3
0.6908	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1778	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