NPASS Compound

Structure

NPC473751 OpenBabel07101718332D 22 22 0 0 1 0 0 0 0 0999 V2000 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -2.5981 -2.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 0.0000 -0.0000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 11 2 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 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:	306.15
Volume:	322.164
LogP:	3.765
LogD:	1.565
LogS:	-3.477
# Rotatable Bonds:	7
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	3.079
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.967
MDCK Permeability:	1.280194555874914e-05
Pgp-inhibitor:	0.082
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.231

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	91.97931671142578%
Volume Distribution (VD):	0.468
Pgp-substrate:	11.85596752166748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	6.916
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.097
Carcinogencity:	0.059
Eye Corrosion:	0.004
Eye Irritation:	0.233
Respiratory Toxicity:	0.101

Download Data

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

Natural Product: NPC473751

Natural Product ID:	NPC473751
*Common Name:**	Crassinervic Acid
IUPAC Name:	4-hydroxy-3-(3-hydroxy-3,7-dimethyloct-6-enoyl)benzoic acid
Synonyms:	crassinervic acid
Standard InCHIKey:	YHANYRDRFGGDNZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-11(2)5-4-8-17(3,22)10-15(19)13-9-12(16(20)21)6-7-14(13)18/h5-7,9,18,22H,4,8,10H2,1-3H3,(H,20,21)
SMILES:	CC(=CCCC(CC(=O)c1cc(ccc1O)C(=O)O)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450857
PubChem CID:	11324217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33179	piper sp.	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568762]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	0.5	ug	PMID[531153]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	0.5	ug	PMID[531153]

☑ 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 NPC473751 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	289
0.1-0.2	1459
0.2-0.3	3609
0.3-0.4	9327
0.4-0.5	10115
0.5-0.6	5715
0.6-0.7	7797
0.7-0.8	3946
0.8-0.85	347
0.85-0.9	85
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9244	High Similarity	NPC273282
0.9244	High Similarity	NPC474890
0.9244	High Similarity	NPC161943
0.9076	High Similarity	NPC83718
0.8976	High Similarity	NPC474998
0.896	High Similarity	NPC475733
0.8898	High Similarity	NPC21305
0.8872	High Similarity	NPC473988
0.8871	High Similarity	NPC91105
0.8871	High Similarity	NPC475192
0.8871	High Similarity	NPC309765
0.8824	High Similarity	NPC242136
0.8819	High Similarity	NPC103356
0.8819	High Similarity	NPC100067
0.8819	High Similarity	NPC30501
0.8819	High Similarity	NPC98254
0.8819	High Similarity	NPC105157
0.8819	High Similarity	NPC23126
0.8819	High Similarity	NPC72158
0.8819	High Similarity	NPC162612
0.8819	High Similarity	NPC190043
0.8819	High Similarity	NPC169250
0.8819	High Similarity	NPC266689
0.88	High Similarity	NPC65761
0.88	High Similarity	NPC472029
0.88	High Similarity	NPC174991
0.879	High Similarity	NPC215392
0.879	High Similarity	NPC303737
0.879	High Similarity	NPC226275
0.875	High Similarity	NPC221777
0.875	High Similarity	NPC473017
0.874	High Similarity	NPC267846
0.874	High Similarity	NPC62952
0.872	High Similarity	NPC67300
0.871	High Similarity	NPC149246
0.8702	High Similarity	NPC48036
0.8672	High Similarity	NPC116513
0.8647	High Similarity	NPC475955
0.8647	High Similarity	NPC474726
0.8615	High Similarity	NPC17840
0.8615	High Similarity	NPC247477
0.8605	High Similarity	NPC473744
0.8605	High Similarity	NPC95537
0.8605	High Similarity	NPC229894
0.8605	High Similarity	NPC41263
0.8583	High Similarity	NPC184219
0.8561	High Similarity	NPC37299
0.8561	High Similarity	NPC139074
0.8561	High Similarity	NPC180261
0.8561	High Similarity	NPC40524
0.8561	High Similarity	NPC213485
0.856	High Similarity	NPC146642
0.855	High Similarity	NPC275504
0.855	High Similarity	NPC473777
0.855	High Similarity	NPC475042
0.8548	High Similarity	NPC161617
0.8548	High Similarity	NPC473767
0.8538	High Similarity	NPC117899
0.8529	High Similarity	NPC315578
0.8527	High Similarity	NPC121104
0.8519	High Similarity	NPC13715
0.8519	High Similarity	NPC9121
0.8519	High Similarity	NPC4214
0.8519	High Similarity	NPC177307
0.8519	High Similarity	NPC112135
0.8512	High Similarity	NPC211421
0.8507	High Similarity	NPC118919
0.8504	High Similarity	NPC477153
0.8496	Intermediate Similarity	NPC166480
0.8496	Intermediate Similarity	NPC282780
0.8487	Intermediate Similarity	NPC95172
0.8485	Intermediate Similarity	NPC302844
0.848	Intermediate Similarity	NPC294037
0.8468	Intermediate Similarity	NPC209486
0.8468	Intermediate Similarity	NPC241089
0.8468	Intermediate Similarity	NPC40649
0.8462	Intermediate Similarity	NPC193203
0.8456	Intermediate Similarity	NPC19622
0.8456	Intermediate Similarity	NPC112789
0.8456	Intermediate Similarity	NPC162939
0.8456	Intermediate Similarity	NPC26924
0.8444	Intermediate Similarity	NPC471452
0.8444	Intermediate Similarity	NPC178467
0.8444	Intermediate Similarity	NPC474771
0.8444	Intermediate Similarity	NPC149372
0.8444	Intermediate Similarity	NPC65837
0.8444	Intermediate Similarity	NPC474849
0.8433	Intermediate Similarity	NPC283590
0.8433	Intermediate Similarity	NPC290803
0.8433	Intermediate Similarity	NPC70859
0.8433	Intermediate Similarity	NPC470210
0.8433	Intermediate Similarity	NPC61153
0.8433	Intermediate Similarity	NPC477596
0.8433	Intermediate Similarity	NPC130899
0.8425	Intermediate Similarity	NPC68167
0.8425	Intermediate Similarity	NPC133909
0.8425	Intermediate Similarity	NPC32032
0.8409	Intermediate Similarity	NPC18798
0.8403	Intermediate Similarity	NPC224584
0.8397	Intermediate Similarity	NPC476119
0.8394	Intermediate Similarity	NPC275903
0.8387	Intermediate Similarity	NPC121259
0.8385	Intermediate Similarity	NPC293387
0.8382	Intermediate Similarity	NPC475974
0.8382	Intermediate Similarity	NPC472403
0.8372	Intermediate Similarity	NPC477454
0.8372	Intermediate Similarity	NPC262671
0.8372	Intermediate Similarity	NPC201728
0.837	Intermediate Similarity	NPC65005
0.837	Intermediate Similarity	NPC194764
0.837	Intermediate Similarity	NPC264112
0.8358	Intermediate Similarity	NPC477594
0.8358	Intermediate Similarity	NPC204582
0.8358	Intermediate Similarity	NPC288089
0.8346	Intermediate Similarity	NPC196976
0.8346	Intermediate Similarity	NPC242895
0.8346	Intermediate Similarity	NPC115159
0.8346	Intermediate Similarity	NPC45438
0.8346	Intermediate Similarity	NPC267552
0.8346	Intermediate Similarity	NPC73532
0.8346	Intermediate Similarity	NPC224273
0.8346	Intermediate Similarity	NPC156139
0.8346	Intermediate Similarity	NPC175738
0.8346	Intermediate Similarity	NPC143427
0.8346	Intermediate Similarity	NPC19174
0.8333	Intermediate Similarity	NPC16455
0.8333	Intermediate Similarity	NPC470987
0.8333	Intermediate Similarity	NPC313123
0.8333	Intermediate Similarity	NPC478201
0.8333	Intermediate Similarity	NPC21378
0.8333	Intermediate Similarity	NPC307990
0.8333	Intermediate Similarity	NPC478217
0.8333	Intermediate Similarity	NPC472035
0.8321	Intermediate Similarity	NPC21350
0.8319	Intermediate Similarity	NPC29883
0.8319	Intermediate Similarity	NPC226699
0.8309	Intermediate Similarity	NPC194579
0.8308	Intermediate Similarity	NPC8745
0.8308	Intermediate Similarity	NPC473691
0.8308	Intermediate Similarity	NPC95309
0.8306	Intermediate Similarity	NPC477453
0.8296	Intermediate Similarity	NPC80035
0.8296	Intermediate Similarity	NPC278375
0.8295	Intermediate Similarity	NPC13238
0.8284	Intermediate Similarity	NPC470988
0.8284	Intermediate Similarity	NPC43627
0.8284	Intermediate Similarity	NPC115458
0.8281	Intermediate Similarity	NPC232708
0.8281	Intermediate Similarity	NPC297193
0.8273	Intermediate Similarity	NPC193555
0.8271	Intermediate Similarity	NPC198249
0.8268	Intermediate Similarity	NPC26433
0.8268	Intermediate Similarity	NPC222876
0.8268	Intermediate Similarity	NPC244994
0.8268	Intermediate Similarity	NPC178395
0.8268	Intermediate Similarity	NPC159760
0.8268	Intermediate Similarity	NPC179092
0.8268	Intermediate Similarity	NPC272454
0.8268	Intermediate Similarity	NPC35856
0.8268	Intermediate Similarity	NPC301987
0.8268	Intermediate Similarity	NPC292665
0.8268	Intermediate Similarity	NPC115188
0.8268	Intermediate Similarity	NPC297186
0.8261	Intermediate Similarity	NPC470986
0.8258	Intermediate Similarity	NPC92624
0.8258	Intermediate Similarity	NPC109123
0.8258	Intermediate Similarity	NPC99731
0.8258	Intermediate Similarity	NPC473019
0.8254	Intermediate Similarity	NPC184579
0.8254	Intermediate Similarity	NPC233165
0.8248	Intermediate Similarity	NPC221104
0.8248	Intermediate Similarity	NPC317119
0.824	Intermediate Similarity	NPC269414
0.8235	Intermediate Similarity	NPC184658
0.8235	Intermediate Similarity	NPC6984
0.8235	Intermediate Similarity	NPC131039
0.8231	Intermediate Similarity	NPC10926
0.8226	Intermediate Similarity	NPC161304
0.8226	Intermediate Similarity	NPC322197
0.8222	Intermediate Similarity	NPC475088
0.8222	Intermediate Similarity	NPC474519
0.8222	Intermediate Similarity	NPC470984
0.8222	Intermediate Similarity	NPC474097
0.8217	Intermediate Similarity	NPC306288
0.8214	Intermediate Similarity	NPC478202
0.8214	Intermediate Similarity	NPC66593
0.8209	Intermediate Similarity	NPC185624
0.8201	Intermediate Similarity	NPC470842
0.8201	Intermediate Similarity	NPC290550
0.8197	Intermediate Similarity	NPC114682
0.8195	Intermediate Similarity	NPC327457
0.8195	Intermediate Similarity	NPC259942
0.8195	Intermediate Similarity	NPC109778
0.8195	Intermediate Similarity	NPC86774
0.8194	Intermediate Similarity	NPC315520
0.8189	Intermediate Similarity	NPC159525
0.8188	Intermediate Similarity	NPC138099
0.8188	Intermediate Similarity	NPC242994
0.8188	Intermediate Similarity	NPC474655
0.8182	Intermediate Similarity	NPC470981

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 NPC473751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	942
0.2-0.3	1557
0.3-0.4	2623
0.4-0.5	2148
0.5-0.6	1101
0.6-0.7	393
0.7-0.8	98
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1164	Approved
0.8129	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD9266	Approved
0.8099	Intermediate Similarity	NPD74	Approved
0.8043	Intermediate Similarity	NPD2935	Discontinued
0.8043	Intermediate Similarity	NPD5408	Approved
0.8043	Intermediate Similarity	NPD5404	Approved
0.8043	Intermediate Similarity	NPD5405	Approved
0.8043	Intermediate Similarity	NPD5406	Approved
0.8031	Intermediate Similarity	NPD9545	Approved
0.8017	Intermediate Similarity	NPD9264	Approved
0.8017	Intermediate Similarity	NPD9263	Approved
0.8017	Intermediate Similarity	NPD9267	Approved
0.8016	Intermediate Similarity	NPD9493	Approved
0.7971	Intermediate Similarity	NPD2799	Discontinued
0.7971	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1470	Approved
0.7941	Intermediate Similarity	NPD943	Approved
0.7923	Intermediate Similarity	NPD1201	Approved
0.7891	Intermediate Similarity	NPD7411	Suspended
0.781	Intermediate Similarity	NPD1240	Approved
0.7734	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD9281	Approved
0.7714	Intermediate Similarity	NPD1510	Phase 2
0.7698	Intermediate Similarity	NPD1607	Approved
0.7686	Intermediate Similarity	NPD9261	Approved
0.7664	Intermediate Similarity	NPD3764	Approved
0.7664	Intermediate Similarity	NPD2313	Discontinued
0.7655	Intermediate Similarity	NPD7390	Discontinued
0.7635	Intermediate Similarity	NPD3226	Approved
0.7632	Intermediate Similarity	NPD7075	Discontinued
0.7594	Intermediate Similarity	NPD9717	Approved
0.7589	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7819	Suspended
0.755	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2798	Approved
0.7483	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7467	Intermediate Similarity	NPD4380	Phase 2
0.7463	Intermediate Similarity	NPD9269	Phase 2
0.7448	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1549	Phase 2
0.7426	Intermediate Similarity	NPD1203	Approved
0.7424	Intermediate Similarity	NPD9268	Approved
0.7415	Intermediate Similarity	NPD6799	Approved
0.7379	Intermediate Similarity	NPD1243	Approved
0.7368	Intermediate Similarity	NPD6801	Discontinued
0.7361	Intermediate Similarity	NPD2346	Discontinued
0.7361	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7768	Phase 2
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7329	Intermediate Similarity	NPD3750	Approved
0.7324	Intermediate Similarity	NPD6651	Approved
0.732	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2796	Approved
0.729	Intermediate Similarity	NPD3749	Approved
0.7286	Intermediate Similarity	NPD3268	Approved
0.7285	Intermediate Similarity	NPD7458	Discontinued
0.7279	Intermediate Similarity	NPD2309	Approved
0.726	Intermediate Similarity	NPD2800	Approved
0.7258	Intermediate Similarity	NPD1930	Approved
0.7258	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1929	Approved
0.7254	Intermediate Similarity	NPD230	Phase 1
0.7237	Intermediate Similarity	NPD6599	Discontinued
0.723	Intermediate Similarity	NPD3300	Phase 2
0.7215	Intermediate Similarity	NPD6232	Discontinued
0.7211	Intermediate Similarity	NPD7003	Approved
0.7188	Intermediate Similarity	NPD7473	Discontinued
0.7177	Intermediate Similarity	NPD940	Approved
0.7177	Intermediate Similarity	NPD846	Approved
0.7176	Intermediate Similarity	NPD5951	Approved
0.7172	Intermediate Similarity	NPD1551	Phase 2
0.7163	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7133	Intermediate Similarity	NPD447	Suspended
0.7133	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD256	Approved
0.7121	Intermediate Similarity	NPD255	Approved
0.7117	Intermediate Similarity	NPD5953	Discontinued
0.7114	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD520	Approved
0.7111	Intermediate Similarity	NPD3019	Approved
0.7111	Intermediate Similarity	NPD2932	Approved
0.7111	Intermediate Similarity	NPD4626	Approved
0.7103	Intermediate Similarity	NPD4308	Phase 3
0.7095	Intermediate Similarity	NPD3400	Discontinued
0.708	Intermediate Similarity	NPD3972	Approved
0.707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1511	Approved
0.7059	Intermediate Similarity	NPD9258	Approved
0.7059	Intermediate Similarity	NPD9256	Approved
0.7049	Intermediate Similarity	NPD2859	Approved
0.7049	Intermediate Similarity	NPD2860	Approved
0.7049	Intermediate Similarity	NPD1809	Phase 2
0.7042	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1934	Approved
0.7025	Intermediate Similarity	NPD845	Approved
0.702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3020	Approved
0.7006	Intermediate Similarity	NPD3882	Suspended
0.6994	Remote Similarity	NPD7286	Phase 2
0.6987	Remote Similarity	NPD2801	Approved
0.6986	Remote Similarity	NPD3748	Approved
0.6986	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7033	Discontinued
0.698	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5049	Phase 3
0.6974	Remote Similarity	NPD1512	Approved
0.6967	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2933	Approved
0.6967	Remote Similarity	NPD2934	Approved
0.6963	Remote Similarity	NPD1759	Phase 1
0.6957	Remote Similarity	NPD1608	Approved
0.6943	Remote Similarity	NPD3817	Phase 2
0.6933	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2354	Approved
0.6929	Remote Similarity	NPD3266	Approved
0.6929	Remote Similarity	NPD2797	Approved
0.6929	Remote Similarity	NPD3267	Approved
0.6911	Remote Similarity	NPD844	Approved
0.6903	Remote Similarity	NPD6585	Discontinued
0.6892	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1471	Phase 3
0.689	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1758	Phase 1
0.6884	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2066	Phase 3
0.6879	Remote Similarity	NPD1019	Discontinued
0.6879	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8166	Discontinued
0.6861	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1283	Approved
0.6842	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6959	Discontinued
0.6831	Remote Similarity	NPD9494	Approved
0.6828	Remote Similarity	NPD4307	Phase 2
0.6821	Remote Similarity	NPD6190	Approved
0.6818	Remote Similarity	NPD5403	Approved
0.6815	Remote Similarity	NPD9568	Approved
0.6813	Remote Similarity	NPD919	Approved
0.68	Remote Similarity	NPD2654	Approved
0.6797	Remote Similarity	NPD1237	Approved
0.6792	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD690	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5711	Approved
0.679	Remote Similarity	NPD5710	Approved
0.6788	Remote Similarity	NPD5691	Approved
0.6786	Remote Similarity	NPD1755	Approved
0.6781	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2353	Approved
0.6779	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6559	Discontinued
0.6765	Remote Similarity	NPD8150	Discontinued
0.6763	Remote Similarity	NPD422	Phase 1
0.6761	Remote Similarity	NPD258	Approved
0.6761	Remote Similarity	NPD257	Approved
0.6759	Remote Similarity	NPD6663	Approved
0.6752	Remote Similarity	NPD5889	Approved
0.6752	Remote Similarity	NPD5890	Approved
0.6748	Remote Similarity	NPD1202	Approved
0.6748	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5048	Discontinued
0.6739	Remote Similarity	NPD17	Approved
0.6738	Remote Similarity	NPD3225	Approved
0.6738	Remote Similarity	NPD1876	Approved
0.673	Remote Similarity	NPD2296	Approved
0.6727	Remote Similarity	NPD3818	Discontinued
0.6723	Remote Similarity	NPD9257	Approved
0.6723	Remote Similarity	NPD9259	Approved
0.672	Remote Similarity	NPD288	Approved
0.6716	Remote Similarity	NPD1241	Discontinued
0.6714	Remote Similarity	NPD1481	Phase 2
0.6713	Remote Similarity	NPD5736	Approved
0.6711	Remote Similarity	NPD4477	Approved
0.6711	Remote Similarity	NPD3887	Approved
0.6711	Remote Similarity	NPD4476	Approved
0.671	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6166	Phase 2
0.6707	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3847	Discontinued
0.6691	Remote Similarity	NPD3026	Approved
0.6691	Remote Similarity	NPD3023	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