NPASS Compound

Structure

NPC472222 OpenBabel07101718252D 21 22 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -0.8660 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 13 2 1 6 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	503.349
LogP:	5.153
LogD:	4.367
LogS:	-5.442
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	5.954
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.047
MDCK Permeability:	2.3138898541219532e-05
Pgp-inhibitor:	0.767
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.595
30% Bioavailability (F30%):	0.309

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.821
Plasma Protein Binding (PPB):	89.82831573486328%
Volume Distribution (VD):	1.223
Pgp-substrate:	5.49390983581543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.294
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	13.358
Half-life (T1/2):	0.108

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.608
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.334
Carcinogencity:	0.756
Eye Corrosion:	0.004
Eye Irritation:	0.06
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC472222

Natural Product ID:	NPC472222
*Common Name:**	Tanzawaic Acid D
IUPAC Name:	(2E,4E)-5-[(6R,8R)-6-hydroxy-2,6,8-trimethyl-7,8-dihydro-5H-naphthalen-1-yl]penta-2,4-dienoic acid
Synonyms:
Standard InCHIKey:	WGCSETPVPVTTSA-WHVXERDFSA-N
Standard InCHI:	InChI=1S/C18H22O3/c1-12-8-9-14-11-18(3,21)10-13(2)17(14)15(12)6-4-5-7-16(19)20/h4-9,13,21H,10-11H2,1-3H3,(H,19,20)/b6-4+,7-5+/t13-,18-/m1/s1
SMILES:	OC(=O)/C=C/C=C/c1c(C)ccc2c1[C@H](C)C[C@@](C2)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353036
PubChem CID:	10401745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO33154	penicillium sp. sf-6013	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453820]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	24.1	%	PMID[500161]

☑ 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 NPC472222 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	211
0.1-0.2	1271
0.2-0.3	2430
0.3-0.4	8528
0.4-0.5	14597
0.5-0.6	12052
0.6-0.7	3180
0.7-0.8	404
0.8-0.85	17
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472221
0.9412	High Similarity	NPC133308
0.8879	High Similarity	NPC186933
0.875	High Similarity	NPC26224
0.8505	High Similarity	NPC475002
0.8505	High Similarity	NPC95126
0.8426	Intermediate Similarity	NPC66208
0.835	Intermediate Similarity	NPC469481
0.835	Intermediate Similarity	NPC225079
0.8224	Intermediate Similarity	NPC27252
0.8224	Intermediate Similarity	NPC472980
0.8224	Intermediate Similarity	NPC472979
0.819	Intermediate Similarity	NPC19856
0.8165	Intermediate Similarity	NPC474057
0.8148	Intermediate Similarity	NPC318327
0.8103	Intermediate Similarity	NPC269923
0.8103	Intermediate Similarity	NPC167323
0.8053	Intermediate Similarity	NPC105141
0.8053	Intermediate Similarity	NPC242764
0.8053	Intermediate Similarity	NPC212891
0.8037	Intermediate Similarity	NPC243601
0.8036	Intermediate Similarity	NPC93181
0.8036	Intermediate Similarity	NPC221275
0.8019	Intermediate Similarity	NPC247976
0.8019	Intermediate Similarity	NPC329556
0.8	Intermediate Similarity	NPC133809
0.8	Intermediate Similarity	NPC128248
0.8	Intermediate Similarity	NPC136810
0.7982	Intermediate Similarity	NPC472982
0.7982	Intermediate Similarity	NPC475006
0.7982	Intermediate Similarity	NPC149455
0.7982	Intermediate Similarity	NPC64642
0.7966	Intermediate Similarity	NPC85511
0.7963	Intermediate Similarity	NPC142326
0.7963	Intermediate Similarity	NPC94751
0.7959	Intermediate Similarity	NPC474211
0.7949	Intermediate Similarity	NPC293831
0.7949	Intermediate Similarity	NPC369
0.7946	Intermediate Similarity	NPC471721
0.7938	Intermediate Similarity	NPC267704
0.7931	Intermediate Similarity	NPC133389
0.7931	Intermediate Similarity	NPC183339
0.7931	Intermediate Similarity	NPC234337
0.7925	Intermediate Similarity	NPC304873
0.7895	Intermediate Similarity	NPC470820
0.787	Intermediate Similarity	NPC243677
0.787	Intermediate Similarity	NPC105899
0.7863	Intermediate Similarity	NPC241001
0.7857	Intermediate Similarity	NPC474354
0.7857	Intermediate Similarity	NPC93287
0.785	Intermediate Similarity	NPC255676
0.7826	Intermediate Similarity	NPC45794
0.7818	Intermediate Similarity	NPC470039
0.7815	Intermediate Similarity	NPC275145
0.7815	Intermediate Similarity	NPC77691
0.7812	Intermediate Similarity	NPC242628
0.7798	Intermediate Similarity	NPC100767
0.7798	Intermediate Similarity	NPC37914
0.7778	Intermediate Similarity	NPC329282
0.7778	Intermediate Similarity	NPC478121
0.7768	Intermediate Similarity	NPC292834
0.7768	Intermediate Similarity	NPC471188
0.7768	Intermediate Similarity	NPC111108
0.7759	Intermediate Similarity	NPC328694
0.7759	Intermediate Similarity	NPC254233
0.7757	Intermediate Similarity	NPC25458
0.7755	Intermediate Similarity	NPC168855
0.775	Intermediate Similarity	NPC265413
0.775	Intermediate Similarity	NPC10154
0.7748	Intermediate Similarity	NPC273837
0.7739	Intermediate Similarity	NPC158157
0.7736	Intermediate Similarity	NPC217621
0.7731	Intermediate Similarity	NPC182333
0.7731	Intermediate Similarity	NPC273336
0.7731	Intermediate Similarity	NPC121168
0.7727	Intermediate Similarity	NPC151477
0.7723	Intermediate Similarity	NPC1793
0.7719	Intermediate Similarity	NPC476357
0.7714	Intermediate Similarity	NPC251579
0.7714	Intermediate Similarity	NPC226041
0.7714	Intermediate Similarity	NPC324602
0.7714	Intermediate Similarity	NPC133135
0.7712	Intermediate Similarity	NPC472981
0.7706	Intermediate Similarity	NPC117115
0.7706	Intermediate Similarity	NPC471133
0.7706	Intermediate Similarity	NPC471186
0.7706	Intermediate Similarity	NPC303141
0.7705	Intermediate Similarity	NPC115797
0.7705	Intermediate Similarity	NPC51448
0.7692	Intermediate Similarity	NPC172925
0.7692	Intermediate Similarity	NPC42657
0.767	Intermediate Similarity	NPC314690
0.767	Intermediate Similarity	NPC128645
0.7658	Intermediate Similarity	NPC11554
0.7647	Intermediate Similarity	NPC86670
0.7647	Intermediate Similarity	NPC162935
0.7647	Intermediate Similarity	NPC274455
0.7647	Intermediate Similarity	NPC70940
0.7647	Intermediate Similarity	NPC249340
0.7642	Intermediate Similarity	NPC229242
0.7623	Intermediate Similarity	NPC253681
0.7623	Intermediate Similarity	NPC5486
0.7615	Intermediate Similarity	NPC315794
0.7615	Intermediate Similarity	NPC56168
0.7611	Intermediate Similarity	NPC471189
0.7589	Intermediate Similarity	NPC58865
0.7586	Intermediate Similarity	NPC471936
0.7573	Intermediate Similarity	NPC220596
0.757	Intermediate Similarity	NPC221825
0.7568	Intermediate Similarity	NPC21929
0.7568	Intermediate Similarity	NPC249811
0.7565	Intermediate Similarity	NPC274839
0.7563	Intermediate Similarity	NPC164852
0.7547	Intermediate Similarity	NPC253423
0.7544	Intermediate Similarity	NPC46940
0.7544	Intermediate Similarity	NPC306977
0.7544	Intermediate Similarity	NPC242957
0.7544	Intermediate Similarity	NPC206414
0.7544	Intermediate Similarity	NPC287055
0.7544	Intermediate Similarity	NPC250323
0.7544	Intermediate Similarity	NPC143768
0.7541	Intermediate Similarity	NPC470765
0.7523	Intermediate Similarity	NPC470202
0.7522	Intermediate Similarity	NPC265513
0.7522	Intermediate Similarity	NPC132720
0.7521	Intermediate Similarity	NPC307139
0.7521	Intermediate Similarity	NPC472373
0.75	Intermediate Similarity	NPC154696
0.75	Intermediate Similarity	NPC50192
0.75	Intermediate Similarity	NPC469719
0.748	Intermediate Similarity	NPC473220
0.748	Intermediate Similarity	NPC470753
0.7478	Intermediate Similarity	NPC196673
0.7478	Intermediate Similarity	NPC715
0.7477	Intermediate Similarity	NPC21594
0.7477	Intermediate Similarity	NPC477251
0.7476	Intermediate Similarity	NPC213156
0.7476	Intermediate Similarity	NPC240108
0.7459	Intermediate Similarity	NPC474532
0.7456	Intermediate Similarity	NPC95716
0.7456	Intermediate Similarity	NPC280789
0.7456	Intermediate Similarity	NPC176279
0.7456	Intermediate Similarity	NPC151537
0.7456	Intermediate Similarity	NPC260323
0.7455	Intermediate Similarity	NPC238696
0.7451	Intermediate Similarity	NPC329064
0.7449	Intermediate Similarity	NPC133050
0.744	Intermediate Similarity	NPC131684
0.7438	Intermediate Similarity	NPC12016
0.7438	Intermediate Similarity	NPC478058
0.7436	Intermediate Similarity	NPC472862
0.7436	Intermediate Similarity	NPC469663
0.7436	Intermediate Similarity	NPC92
0.7436	Intermediate Similarity	NPC471668
0.7434	Intermediate Similarity	NPC75272
0.7434	Intermediate Similarity	NPC471954
0.7426	Intermediate Similarity	NPC93843
0.7417	Intermediate Similarity	NPC259703
0.7417	Intermediate Similarity	NPC32322
0.7414	Intermediate Similarity	NPC195922
0.7404	Intermediate Similarity	NPC475059
0.7404	Intermediate Similarity	NPC475023
0.74	Intermediate Similarity	NPC95429
0.7398	Intermediate Similarity	NPC275576
0.7398	Intermediate Similarity	NPC45821
0.7395	Intermediate Similarity	NPC202015
0.7395	Intermediate Similarity	NPC476645
0.7395	Intermediate Similarity	NPC151197
0.7391	Intermediate Similarity	NPC128368
0.7391	Intermediate Similarity	NPC470253
0.7391	Intermediate Similarity	NPC228988
0.7391	Intermediate Similarity	NPC471179
0.7387	Intermediate Similarity	NPC172483
0.7383	Intermediate Similarity	NPC289201
0.7379	Intermediate Similarity	NPC199567
0.7377	Intermediate Similarity	NPC12881
0.7377	Intermediate Similarity	NPC328107
0.7377	Intermediate Similarity	NPC140118
0.7377	Intermediate Similarity	NPC470815
0.7377	Intermediate Similarity	NPC318067
0.7377	Intermediate Similarity	NPC12824
0.7373	Intermediate Similarity	NPC477136
0.7373	Intermediate Similarity	NPC84129
0.7373	Intermediate Similarity	NPC278652
0.7368	Intermediate Similarity	NPC13482
0.7368	Intermediate Similarity	NPC141782
0.736	Intermediate Similarity	NPC96024
0.736	Intermediate Similarity	NPC93632
0.7353	Intermediate Similarity	NPC322387
0.735	Intermediate Similarity	NPC192948
0.735	Intermediate Similarity	NPC35797
0.7339	Intermediate Similarity	NPC289117
0.7339	Intermediate Similarity	NPC264728
0.7339	Intermediate Similarity	NPC169913
0.7339	Intermediate Similarity	NPC72729
0.7333	Intermediate Similarity	NPC475057
0.7333	Intermediate Similarity	NPC470585
0.7323	Intermediate Similarity	NPC191395
0.7321	Intermediate Similarity	NPC136962
0.7321	Intermediate Similarity	NPC83409

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 NPC472222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	939
0.2-0.3	1244
0.3-0.4	2843
0.4-0.5	2425
0.5-0.6	1159
0.6-0.7	293
0.7-0.8	43
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD2066	Phase 3
0.8218	Intermediate Similarity	NPD6049	Phase 2
0.8218	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD5951	Approved
0.8021	Intermediate Similarity	NPD3971	Phase 1
0.8019	Intermediate Similarity	NPD1929	Approved
0.8019	Intermediate Similarity	NPD1930	Approved
0.8019	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1090	Approved
0.7647	Intermediate Similarity	NPD1089	Approved
0.7647	Intermediate Similarity	NPD1086	Approved
0.7627	Intermediate Similarity	NPD4626	Approved
0.7596	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD800	Approved
0.7544	Intermediate Similarity	NPD7635	Approved
0.7524	Intermediate Similarity	NPD1693	Approved
0.7522	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1088	Approved
0.7455	Intermediate Similarity	NPD5909	Discontinued
0.7431	Intermediate Similarity	NPD1932	Approved
0.7407	Intermediate Similarity	NPD3020	Approved
0.7404	Intermediate Similarity	NPD1239	Approved
0.7383	Intermediate Similarity	NPD1566	Phase 3
0.7383	Intermediate Similarity	NPD1565	Approved
0.7383	Intermediate Similarity	NPD1564	Approved
0.7364	Intermediate Similarity	NPD6647	Phase 2
0.7353	Intermediate Similarity	NPD1087	Approved
0.735	Intermediate Similarity	NPD4198	Discontinued
0.7345	Intermediate Similarity	NPD2329	Discontinued
0.7328	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7008	Discontinued
0.7265	Intermediate Similarity	NPD2629	Approved
0.7257	Intermediate Similarity	NPD2342	Discontinued
0.725	Intermediate Similarity	NPD5691	Approved
0.7227	Intermediate Similarity	NPD7610	Discontinued
0.719	Intermediate Similarity	NPD2932	Approved
0.719	Intermediate Similarity	NPD3019	Approved
0.7188	Intermediate Similarity	NPD9716	Approved
0.7177	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD5736	Approved
0.713	Intermediate Similarity	NPD1989	Approved
0.713	Intermediate Similarity	NPD2859	Approved
0.713	Intermediate Similarity	NPD2860	Approved
0.7103	Intermediate Similarity	NPD845	Approved
0.7103	Intermediate Similarity	NPD1563	Approved
0.7064	Intermediate Similarity	NPD288	Approved
0.7064	Intermediate Similarity	NPD3495	Discontinued
0.7049	Intermediate Similarity	NPD4059	Approved
0.7048	Intermediate Similarity	NPD5347	Phase 2
0.7048	Intermediate Similarity	NPD5346	Phase 2
0.7037	Intermediate Similarity	NPD2933	Approved
0.7037	Intermediate Similarity	NPD2934	Approved
0.7027	Intermediate Similarity	NPD1616	Discontinued
0.7025	Intermediate Similarity	NPD3091	Approved
0.7	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5404	Approved
0.6992	Remote Similarity	NPD5406	Approved
0.6992	Remote Similarity	NPD5408	Approved
0.6992	Remote Similarity	NPD5405	Approved
0.6983	Remote Similarity	NPD3022	Approved
0.6983	Remote Similarity	NPD3021	Approved
0.6981	Remote Similarity	NPD9256	Approved
0.6981	Remote Similarity	NPD9258	Approved
0.6972	Remote Similarity	NPD844	Approved
0.6964	Remote Similarity	NPD4817	Approved
0.6964	Remote Similarity	NPD4818	Approved
0.6961	Remote Similarity	NPD9491	Approved
0.696	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD1101	Approved
0.6935	Remote Similarity	NPD5618	Discontinued
0.6935	Remote Similarity	NPD1281	Approved
0.6931	Remote Similarity	NPD226	Approved
0.6923	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6663	Approved
0.6917	Remote Similarity	NPD3317	Approved
0.6912	Remote Similarity	NPD7003	Approved
0.6911	Remote Similarity	NPD2345	Approved
0.6903	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7009	Phase 2
0.6881	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4060	Phase 1
0.6857	Remote Similarity	NPD4793	Discontinued
0.6852	Remote Similarity	NPD7631	Approved
0.6847	Remote Similarity	NPD5926	Approved
0.6842	Remote Similarity	NPD1237	Approved
0.6838	Remote Similarity	NPD5236	Approved
0.6838	Remote Similarity	NPD5235	Approved
0.6838	Remote Similarity	NPD5237	Approved
0.6838	Remote Similarity	NPD5239	Approved
0.6838	Remote Similarity	NPD1317	Discontinued
0.6838	Remote Similarity	NPD5240	Approved
0.6838	Remote Similarity	NPD4750	Phase 3
0.6818	Remote Similarity	NPD1809	Phase 2
0.6807	Remote Similarity	NPD6858	Approved
0.6807	Remote Similarity	NPD7094	Approved
0.68	Remote Similarity	NPD3092	Approved
0.6797	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7961	Discontinued
0.6789	Remote Similarity	NPD1202	Approved
0.6783	Remote Similarity	NPD5048	Discontinued
0.6774	Remote Similarity	NPD2286	Discontinued
0.6774	Remote Similarity	NPD5126	Approved
0.6774	Remote Similarity	NPD5125	Phase 3
0.6774	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5306	Approved
0.6774	Remote Similarity	NPD3095	Discontinued
0.6774	Remote Similarity	NPD5305	Approved
0.6769	Remote Similarity	NPD6966	Discovery
0.6759	Remote Similarity	NPD7609	Phase 3
0.6754	Remote Similarity	NPD4229	Approved
0.6754	Remote Similarity	NPD3680	Approved
0.6754	Remote Similarity	NPD3682	Approved
0.6754	Remote Similarity	NPD4231	Approved
0.6752	Remote Similarity	NPD2182	Approved
0.675	Remote Similarity	NPD2229	Approved
0.675	Remote Similarity	NPD2228	Approved
0.675	Remote Similarity	NPD2234	Approved
0.6748	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7741	Discontinued
0.6746	Remote Similarity	NPD4878	Approved
0.6742	Remote Similarity	NPD4140	Approved
0.672	Remote Similarity	NPD3023	Approved
0.672	Remote Similarity	NPD3026	Approved
0.6719	Remote Similarity	NPD1164	Approved
0.6718	Remote Similarity	NPD3764	Approved
0.6696	Remote Similarity	NPD164	Approved
0.6696	Remote Similarity	NPD9495	Approved
0.6695	Remote Similarity	NPD1792	Phase 2
0.6694	Remote Similarity	NPD4102	Approved
0.6694	Remote Similarity	NPD4093	Discontinued
0.6694	Remote Similarity	NPD1651	Approved
0.6694	Remote Similarity	NPD3025	Approved
0.6694	Remote Similarity	NPD3024	Approved
0.6694	Remote Similarity	NPD4105	Approved
0.6694	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD1201	Approved
0.664	Remote Similarity	NPD4199	Phase 3
0.664	Remote Similarity	NPD1751	Approved
0.6639	Remote Similarity	NPD3643	Approved
0.6639	Remote Similarity	NPD3644	Approved
0.6639	Remote Similarity	NPD2201	Approved
0.6639	Remote Similarity	NPD3642	Approved
0.6636	Remote Similarity	NPD1409	Phase 3
0.6634	Remote Similarity	NPD227	Approved
0.6634	Remote Similarity	NPD225	Approved
0.6619	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD2979	Phase 3
0.6613	Remote Similarity	NPD4479	Discontinued
0.6612	Remote Similarity	NPD6010	Discontinued
0.6609	Remote Similarity	NPD4656	Approved
0.6609	Remote Similarity	NPD3681	Approved
0.6609	Remote Similarity	NPD5765	Approved
0.6609	Remote Similarity	NPD3683	Approved
0.6609	Remote Similarity	NPD4658	Approved
0.6604	Remote Similarity	NPD9257	Approved
0.6604	Remote Similarity	NPD9259	Approved
0.6589	Remote Similarity	NPD2797	Approved
0.6589	Remote Similarity	NPD3094	Phase 2
0.6589	Remote Similarity	NPD1470	Approved
0.6587	Remote Similarity	NPD4106	Approved
0.6587	Remote Similarity	NPD4136	Approved
0.6587	Remote Similarity	NPD4135	Approved
0.6587	Remote Similarity	NPD4879	Approved
0.6587	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD9508	Approved
0.6583	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3134	Approved
0.6581	Remote Similarity	NPD6685	Approved
0.6579	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7236	Approved
0.6569	Remote Similarity	NPD9490	Approved
0.656	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.656	Remote Similarity	NPD1710	Approved
0.6557	Remote Similarity	NPD497	Approved
0.6552	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD2799	Discontinued
0.6544	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD650	Approved
0.6542	Remote Similarity	NPD1282	Approved
0.6541	Remote Similarity	NPD7714	Approved
0.6541	Remote Similarity	NPD7715	Approved
0.6538	Remote Similarity	NPD4624	Approved
0.6535	Remote Similarity	NPD6287	Discontinued
0.6535	Remote Similarity	NPD9294	Approved
0.6532	Remote Similarity	NPD7644	Approved
0.6529	Remote Similarity	NPD5277	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