NPASS Compound

Structure

NPC473802 OpenBabel07101719252D 45 48 0 0 1 0 0 0 0 0999 V2000 -9.3555 8.3252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4894 5.0641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9460 4.1938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6809 2.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0734 3.8954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8326 7.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3301 6.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8072 5.7731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3048 4.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3253 4.9468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8228 4.1059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2999 3.2503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7975 2.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8180 2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3156 1.5831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3361 1.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8336 0.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8542 0.7715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3771 1.6271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9568 2.6450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3769 3.8700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6932 -0.4078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9665 4.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7493 2.0692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2325 3.3929 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1643 2.0692 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3976 1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4062 1.9110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4466 1.1376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4494 2.3881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2747 0.9403 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9273 0.3201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4640 3.3675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9517 0.2322 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2471 2.4134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4670 1.1376 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5097 -1.3701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8952 0.8008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0223 0.3451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2903 1.8856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4297 -0.5209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8353 1.5246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7137 0.5113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4435 3.3529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 23 2 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 33 1 0 0 0 0 22 37 1 0 0 0 0 24 29 1 0 0 0 0 25 35 1 1 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 27 38 2 0 0 0 0 27 44 1 0 0 0 0 28 30 1 0 0 0 0 28 31 1 0 0 0 0 28 35 1 1 0 0 0 29 36 1 0 0 0 0 29 39 2 0 0 0 0 30 33 1 1 0 0 0 30 40 1 0 0 0 0 31 34 1 1 0 0 0 31 45 1 0 0 0 0 32 34 1 6 0 0 0 32 36 1 0 0 0 0 32 41 1 0 0 0 0 33 23 1 1 0 0 0 33 44 1 0 0 0 0 34 22 1 6 0 0 0 34 45 1 0 0 0 0 35 42 1 1 0 0 0 36 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.39
Volume:	662.916
LogP:	6.131
LogD:	3.935
LogS:	-4.12
# Rotatable Bonds:	17
TPSA:	157.05
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	5.624
Fsp3:	0.778
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983
MDCK Permeability:	3.036729685845785e-05
Pgp-inhibitor:	0.7
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.564
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	97.86451721191406%
Volume Distribution (VD):	1.643
Pgp-substrate:	3.0780727863311768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.672
CYP2C9-inhibitor:	0.367
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	3.936
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.873
Drug-inuced Liver Injury (DILI):	0.481
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.303
Carcinogencity:	0.316
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC473802

Natural Product ID:	NPC473802
*Common Name:**	ZPEHDFQKVPIEDZ-HKSZFHKUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZPEHDFQKVPIEDZ-HKSZFHKUSA-N
Standard InCHI:	InChI=1S/C36H56O9/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-27(38)44-33(23(2)3)21-25(5)35(42)26-20-24(4)29(39)36(26,43)32(41)34(22-37)31(45-34)28(35)30(33)40/h18-20,25-26,28,30-32,37,40-43H,2,6-17,21-22H2,1,3-5H3/b19-18+/t25-,26+,28-,30-,31+,32-,33+,34+,35+,36-/m1/s1
SMILES:	CCCCCCCCCCCCCC=CC(=O)OC1(CC(C2(C3C=C(C(=O)C3(C(C4(C(C2C1O)O4)CO)O)O)C)O)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452218
PubChem CID:	44559847
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]

☑ 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
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.08	nmol	PMID[550472]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.0	/nmol	PMID[550472]

☑ 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 NPC473802 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	260
0.1-0.2	1567
0.2-0.3	4443
0.3-0.4	7246
0.4-0.5	13459
0.5-0.6	9579
0.6-0.7	4858
0.7-0.8	1089
0.8-0.85	82
0.85-0.9	89
0.9-0.95	15
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC473709
0.9912	High Similarity	NPC473919
0.9826	High Similarity	NPC471939
0.9741	High Similarity	NPC471940
0.9417	High Similarity	NPC180902
0.9417	High Similarity	NPC475139
0.9328	High Similarity	NPC236999
0.9262	High Similarity	NPC473548
0.9262	High Similarity	NPC223356
0.9262	High Similarity	NPC100017
0.9262	High Similarity	NPC182266
0.9262	High Similarity	NPC475154
0.9262	High Similarity	NPC471136
0.9262	High Similarity	NPC471137
0.9262	High Similarity	NPC475500
0.925	High Similarity	NPC162495
0.9231	High Similarity	NPC162009
0.9231	High Similarity	NPC257017
0.9153	High Similarity	NPC472399
0.9113	High Similarity	NPC68282
0.9098	High Similarity	NPC474508
0.9098	High Similarity	NPC473485
0.9083	High Similarity	NPC168849
0.9083	High Similarity	NPC475273
0.9068	High Similarity	NPC19464
0.9016	High Similarity	NPC475314
0.9016	High Similarity	NPC475606
0.9016	High Similarity	NPC477189
0.9016	High Similarity	NPC251564
0.9	High Similarity	NPC217901
0.8983	High Similarity	NPC52839
0.8983	High Similarity	NPC472401
0.8917	High Similarity	NPC145238
0.8898	High Similarity	NPC145182
0.8898	High Similarity	NPC471126
0.8898	High Similarity	NPC157252
0.8898	High Similarity	NPC471128
0.8889	High Similarity	NPC124676
0.8889	High Similarity	NPC146280
0.8862	High Similarity	NPC473838
0.8862	High Similarity	NPC475389
0.8814	High Similarity	NPC275696
0.8814	High Similarity	NPC5991
0.8814	High Similarity	NPC22628
0.8814	High Similarity	NPC255081
0.8814	High Similarity	NPC5989
0.8814	High Similarity	NPC471108
0.8729	High Similarity	NPC471125
0.8729	High Similarity	NPC171905
0.8729	High Similarity	NPC472758
0.8729	High Similarity	NPC472397
0.8699	High Similarity	NPC476091
0.8699	High Similarity	NPC476078
0.8655	High Similarity	NPC472667
0.8644	High Similarity	NPC156252
0.8644	High Similarity	NPC10721
0.8583	High Similarity	NPC472759
0.8583	High Similarity	NPC19336
0.8583	High Similarity	NPC329080
0.8583	High Similarity	NPC475885
0.8583	High Similarity	NPC185876
0.8559	High Similarity	NPC234858
0.8559	High Similarity	NPC471127
0.8559	High Similarity	NPC154363
0.8548	High Similarity	NPC270109
0.8547	High Similarity	NPC474937
0.8537	High Similarity	NPC473635
0.8509	High Similarity	NPC474716
0.85	High Similarity	NPC470186
0.85	High Similarity	NPC180640
0.85	High Similarity	NPC236918
0.85	High Similarity	NPC156745
0.8475	Intermediate Similarity	NPC474872
0.8475	Intermediate Similarity	NPC472400
0.8462	Intermediate Similarity	NPC475391
0.8462	Intermediate Similarity	NPC221511
0.8462	Intermediate Similarity	NPC215643
0.8462	Intermediate Similarity	NPC17138
0.8462	Intermediate Similarity	NPC170212
0.8462	Intermediate Similarity	NPC151216
0.8462	Intermediate Similarity	NPC101825
0.8462	Intermediate Similarity	NPC265499
0.8462	Intermediate Similarity	NPC89227
0.8462	Intermediate Similarity	NPC471933
0.843	Intermediate Similarity	NPC143755
0.8417	Intermediate Similarity	NPC472760
0.839	Intermediate Similarity	NPC71889
0.839	Intermediate Similarity	NPC477126
0.839	Intermediate Similarity	NPC472757
0.8387	Intermediate Similarity	NPC222307
0.8387	Intermediate Similarity	NPC293112
0.8376	Intermediate Similarity	NPC96739
0.8376	Intermediate Similarity	NPC474871
0.8376	Intermediate Similarity	NPC260786
0.8376	Intermediate Similarity	NPC174471
0.8374	Intermediate Similarity	NPC11895
0.8374	Intermediate Similarity	NPC469352
0.8361	Intermediate Similarity	NPC310511
0.8333	Intermediate Similarity	NPC153651
0.8333	Intermediate Similarity	NPC475371
0.8333	Intermediate Similarity	NPC231529
0.8333	Intermediate Similarity	NPC474741
0.8306	Intermediate Similarity	NPC81736
0.8306	Intermediate Similarity	NPC172154
0.8293	Intermediate Similarity	NPC170538
0.8279	Intermediate Similarity	NPC472004
0.8276	Intermediate Similarity	NPC29827
0.8261	Intermediate Similarity	NPC470975
0.8261	Intermediate Similarity	NPC470979
0.8261	Intermediate Similarity	NPC103088
0.8246	Intermediate Similarity	NPC475945
0.8246	Intermediate Similarity	NPC475871
0.824	Intermediate Similarity	NPC470973
0.8226	Intermediate Similarity	NPC469789
0.822	Intermediate Similarity	NPC158523
0.822	Intermediate Similarity	NPC475937
0.8205	Intermediate Similarity	NPC273433
0.8205	Intermediate Similarity	NPC471934
0.8203	Intermediate Similarity	NPC470185
0.8197	Intermediate Similarity	NPC211093
0.8197	Intermediate Similarity	NPC77689
0.8197	Intermediate Similarity	NPC473636
0.8197	Intermediate Similarity	NPC473839
0.819	Intermediate Similarity	NPC469558
0.8182	Intermediate Similarity	NPC476712
0.8182	Intermediate Similarity	NPC476713
0.8182	Intermediate Similarity	NPC469684
0.8182	Intermediate Similarity	NPC296822
0.8167	Intermediate Similarity	NPC73314
0.816	Intermediate Similarity	NPC24651
0.8158	Intermediate Similarity	NPC474747
0.8151	Intermediate Similarity	NPC317687
0.8151	Intermediate Similarity	NPC473877
0.8145	Intermediate Similarity	NPC23786
0.8145	Intermediate Similarity	NPC470265
0.8136	Intermediate Similarity	NPC153036
0.813	Intermediate Similarity	NPC142882
0.813	Intermediate Similarity	NPC4548
0.813	Intermediate Similarity	NPC475003
0.813	Intermediate Similarity	NPC251226
0.8115	Intermediate Similarity	NPC311554
0.8115	Intermediate Similarity	NPC257457
0.8115	Intermediate Similarity	NPC284707
0.8115	Intermediate Similarity	NPC251310
0.8099	Intermediate Similarity	NPC474333
0.8099	Intermediate Similarity	NPC477509
0.8099	Intermediate Similarity	NPC270478
0.8099	Intermediate Similarity	NPC476710
0.8099	Intermediate Similarity	NPC476711
0.8099	Intermediate Similarity	NPC470793
0.8095	Intermediate Similarity	NPC225049
0.808	Intermediate Similarity	NPC18945
0.808	Intermediate Similarity	NPC67251
0.808	Intermediate Similarity	NPC91693
0.808	Intermediate Similarity	NPC105926
0.808	Intermediate Similarity	NPC265557
0.8077	Intermediate Similarity	NPC476823
0.807	Intermediate Similarity	NPC474742
0.8067	Intermediate Similarity	NPC317107
0.8065	Intermediate Similarity	NPC67569
0.8065	Intermediate Similarity	NPC102822
0.8065	Intermediate Similarity	NPC470779
0.8065	Intermediate Similarity	NPC159456
0.8065	Intermediate Similarity	NPC4021
0.8065	Intermediate Similarity	NPC477046
0.8062	Intermediate Similarity	NPC34963
0.8062	Intermediate Similarity	NPC471855
0.8051	Intermediate Similarity	NPC42662
0.8051	Intermediate Similarity	NPC163004
0.8047	Intermediate Similarity	NPC35109
0.8047	Intermediate Similarity	NPC470880
0.8047	Intermediate Similarity	NPC470851
0.8034	Intermediate Similarity	NPC26617
0.8033	Intermediate Similarity	NPC475323
0.8033	Intermediate Similarity	NPC122033
0.8033	Intermediate Similarity	NPC471146
0.8033	Intermediate Similarity	NPC287343
0.8033	Intermediate Similarity	NPC475809
0.8033	Intermediate Similarity	NPC239273
0.8033	Intermediate Similarity	NPC98249
0.8033	Intermediate Similarity	NPC134430
0.8033	Intermediate Similarity	NPC470854
0.8033	Intermediate Similarity	NPC474654
0.8033	Intermediate Similarity	NPC58662
0.8033	Intermediate Similarity	NPC53396
0.8033	Intermediate Similarity	NPC97908
0.8031	Intermediate Similarity	NPC298841
0.8031	Intermediate Similarity	NPC470882
0.8031	Intermediate Similarity	NPC473253
0.8017	Intermediate Similarity	NPC238667
0.8016	Intermediate Similarity	NPC8369
0.8016	Intermediate Similarity	NPC469790
0.8016	Intermediate Similarity	NPC470922
0.8016	Intermediate Similarity	NPC476729
0.8	Intermediate Similarity	NPC474709
0.8	Intermediate Similarity	NPC58029
0.8	Intermediate Similarity	NPC269642
0.8	Intermediate Similarity	NPC312833
0.8	Intermediate Similarity	NPC469673
0.8	Intermediate Similarity	NPC222688

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 NPC473802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1946
0.2-0.3	3640
0.3-0.4	2117
0.4-0.5	791
0.5-0.6	292
0.6-0.7	115
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8034	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD6371	Approved
0.7815	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5344	Discontinued
0.7742	Intermediate Similarity	NPD7115	Discovery
0.7698	Intermediate Similarity	NPD6319	Approved
0.7561	Intermediate Similarity	NPD8297	Approved
0.7459	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6648	Approved
0.7368	Intermediate Similarity	NPD7319	Approved
0.736	Intermediate Similarity	NPD4632	Approved
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7328	Intermediate Similarity	NPD7492	Approved
0.7293	Intermediate Similarity	NPD7736	Approved
0.7287	Intermediate Similarity	NPD6054	Approved
0.7281	Intermediate Similarity	NPD6698	Approved
0.7281	Intermediate Similarity	NPD46	Approved
0.7273	Intermediate Similarity	NPD6616	Approved
0.7236	Intermediate Similarity	NPD6899	Approved
0.7236	Intermediate Similarity	NPD6881	Approved
0.7231	Intermediate Similarity	NPD6921	Approved
0.7218	Intermediate Similarity	NPD7078	Approved
0.72	Intermediate Similarity	NPD8130	Phase 1
0.7179	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6373	Approved
0.7177	Intermediate Similarity	NPD6372	Approved
0.7176	Intermediate Similarity	NPD6370	Approved
0.7154	Intermediate Similarity	NPD5697	Approved
0.7154	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD7838	Discovery
0.7121	Intermediate Similarity	NPD8328	Phase 3
0.7121	Intermediate Similarity	NPD7604	Phase 2
0.712	Intermediate Similarity	NPD7102	Approved
0.712	Intermediate Similarity	NPD4634	Approved
0.712	Intermediate Similarity	NPD6883	Approved
0.712	Intermediate Similarity	NPD7290	Approved
0.7099	Intermediate Similarity	NPD8517	Approved
0.7099	Intermediate Similarity	NPD8515	Approved
0.7099	Intermediate Similarity	NPD8513	Phase 3
0.7099	Intermediate Similarity	NPD6015	Approved
0.7099	Intermediate Similarity	NPD8516	Approved
0.7099	Intermediate Similarity	NPD6016	Approved
0.709	Intermediate Similarity	NPD8293	Discontinued
0.7073	Intermediate Similarity	NPD7128	Approved
0.7073	Intermediate Similarity	NPD6675	Approved
0.7073	Intermediate Similarity	NPD6402	Approved
0.7073	Intermediate Similarity	NPD5739	Approved
0.7069	Intermediate Similarity	NPD7983	Approved
0.7063	Intermediate Similarity	NPD6617	Approved
0.7063	Intermediate Similarity	NPD6847	Approved
0.7063	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6009	Approved
0.7045	Intermediate Similarity	NPD5988	Approved
0.704	Intermediate Similarity	NPD6014	Approved
0.704	Intermediate Similarity	NPD6013	Approved
0.704	Intermediate Similarity	NPD6012	Approved
0.7023	Intermediate Similarity	NPD6059	Approved
0.7008	Intermediate Similarity	NPD6053	Discontinued
0.697	Remote Similarity	NPD5983	Phase 2
0.696	Remote Similarity	NPD6011	Approved
0.696	Remote Similarity	NPD7320	Approved
0.696	Remote Similarity	NPD6686	Approved
0.6947	Remote Similarity	NPD7516	Approved
0.6935	Remote Similarity	NPD6008	Approved
0.6897	Remote Similarity	NPD1695	Approved
0.6889	Remote Similarity	NPD6336	Discontinued
0.688	Remote Similarity	NPD5701	Approved
0.687	Remote Similarity	NPD7328	Approved
0.687	Remote Similarity	NPD7327	Approved
0.686	Remote Similarity	NPD7638	Approved
0.6838	Remote Similarity	NPD8074	Phase 3
0.6829	Remote Similarity	NPD5211	Phase 2
0.6803	Remote Similarity	NPD4696	Approved
0.6803	Remote Similarity	NPD5285	Approved
0.6803	Remote Similarity	NPD7640	Approved
0.6803	Remote Similarity	NPD5286	Approved
0.6803	Remote Similarity	NPD7639	Approved
0.6797	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5778	Approved
0.6723	Remote Similarity	NPD5779	Approved
0.672	Remote Similarity	NPD5141	Approved
0.6716	Remote Similarity	NPD8380	Approved
0.6716	Remote Similarity	NPD8033	Approved
0.6716	Remote Similarity	NPD8379	Approved
0.6716	Remote Similarity	NPD8378	Approved
0.6716	Remote Similarity	NPD8335	Approved
0.6716	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD5225	Approved
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD5224	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6643	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7260	Phase 2
0.6642	Remote Similarity	NPD8377	Approved
0.6642	Remote Similarity	NPD8294	Approved
0.664	Remote Similarity	NPD5175	Approved
0.664	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD4755	Approved
0.6618	Remote Similarity	NPD7642	Approved
0.6617	Remote Similarity	NPD6335	Approved
0.6613	Remote Similarity	NPD5223	Approved
0.6613	Remote Similarity	NPD1700	Approved
0.6593	Remote Similarity	NPD7503	Approved
0.6591	Remote Similarity	NPD6274	Approved
0.6585	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD8133	Approved
0.6562	Remote Similarity	NPD4729	Approved
0.6562	Remote Similarity	NPD4730	Approved
0.6555	Remote Similarity	NPD5785	Approved
0.6552	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6033	Approved
0.6541	Remote Similarity	NPD6317	Approved
0.6532	Remote Similarity	NPD4700	Approved
0.6512	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6084	Phase 2
0.6504	Remote Similarity	NPD6083	Phase 2
0.6496	Remote Similarity	NPD7830	Approved
0.6496	Remote Similarity	NPD7829	Approved
0.6493	Remote Similarity	NPD6313	Approved
0.6493	Remote Similarity	NPD6314	Approved
0.6471	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5251	Approved
0.6462	Remote Similarity	NPD5248	Approved
0.6462	Remote Similarity	NPD5247	Approved
0.6462	Remote Similarity	NPD5249	Phase 3
0.6462	Remote Similarity	NPD5250	Approved
0.6423	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5222	Approved
0.6423	Remote Similarity	NPD5221	Approved
0.641	Remote Similarity	NPD5363	Approved
0.6406	Remote Similarity	NPD4768	Approved
0.6406	Remote Similarity	NPD4767	Approved
0.6403	Remote Similarity	NPD8273	Phase 1
0.6371	Remote Similarity	NPD5173	Approved
0.6371	Remote Similarity	NPD7902	Approved
0.6364	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD8338	Approved
0.6357	Remote Similarity	NPD6412	Phase 2
0.6356	Remote Similarity	NPD5786	Approved
0.635	Remote Similarity	NPD6908	Approved
0.635	Remote Similarity	NPD6909	Approved
0.6343	Remote Similarity	NPD6868	Approved
0.6341	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD6101	Approved
0.6333	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5696	Approved
0.6311	Remote Similarity	NPD6399	Phase 3
0.6308	Remote Similarity	NPD5128	Approved
0.6299	Remote Similarity	NPD7632	Discontinued
0.629	Remote Similarity	NPD4697	Phase 3
0.629	Remote Similarity	NPD7839	Suspended
0.6288	Remote Similarity	NPD5215	Approved
0.6288	Remote Similarity	NPD5217	Approved
0.6288	Remote Similarity	NPD5216	Approved
0.6276	Remote Similarity	NPD8415	Approved
0.6271	Remote Similarity	NPD1694	Approved
0.626	Remote Similarity	NPD7748	Approved
0.6257	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6845	Suspended
0.625	Remote Similarity	NPD4754	Approved
0.6233	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6411	Approved
0.623	Remote Similarity	NPD7637	Suspended
0.6213	Remote Similarity	NPD8368	Discontinued
0.6212	Remote Similarity	NPD5135	Approved
0.6212	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5169	Approved
0.621	Remote Similarity	NPD5210	Approved
0.621	Remote Similarity	NPD4629	Approved
0.6207	Remote Similarity	NPD5369	Approved
0.6199	Remote Similarity	NPD8407	Phase 2
0.6198	Remote Similarity	NPD5328	Approved
0.617	Remote Similarity	NPD8451	Approved
0.6168	Remote Similarity	NPD7799	Discontinued
0.6165	Remote Similarity	NPD5127	Approved
0.6154	Remote Similarity	NPD6435	Approved
0.6154	Remote Similarity	NPD4270	Approved
0.6154	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4269	Approved
0.6149	Remote Similarity	NPD6334	Approved
0.6149	Remote Similarity	NPD6333	Approved
0.6129	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7900	Approved
0.6127	Remote Similarity	NPD8434	Phase 2
0.6127	Remote Similarity	NPD8448	Approved
0.6115	Remote Similarity	NPD8444	Approved
0.6111	Remote Similarity	NPD5956	Approved
0.6102	Remote Similarity	NPD7154	Phase 3
0.6102	Remote Similarity	NPD5362	Discontinued
0.6102	Remote Similarity	NPD6110	Phase 1

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