NPASS Compound

Structure

NPC198880 OpenBabel07101718182D 26 28 0 0 1 0 0 0 0 0999 V2000 0.4483 -1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 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 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 2.5000 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 1.7321 3.0000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 3.4641 4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9641 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -1.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 0.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 21 2 0 0 0 0 13 18 1 1 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 6 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 20 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.2
Volume:	373.639
LogP:	1.396
LogD:	0.29
LogS:	-2.41
# Rotatable Bonds:	2
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	4.824
Fsp3:	0.8
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:	-5.713
MDCK Permeability:	3.5936423955718055e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.158
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.4
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	59.36009979248047%
Volume Distribution (VD):	0.352
Pgp-substrate:	28.372594833374023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.375
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.542
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.42
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	1.893
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.087
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.033
Carcinogencity:	0.585
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC198880

Natural Product ID:	NPC198880
*Common Name:**	Aquilarabietic Acid E
IUPAC Name:	(1R,4aS,7S,8R,10aR)-7,8-dihydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthrene-1-carboxylic acid
Synonyms:	Aquilarabietic acid E
Standard InCHIKey:	UBGDAOTWVMIAKV-VMGFOFSFSA-N
Standard InCHI:	InChI=1S/C20H30O6/c1-17(2,25)20(26)9-6-11-14(15(20)22)12(21)10-13-18(11,3)7-5-8-19(13,4)16(23)24/h13,15,22,25-26H,5-10H2,1-4H3,(H,23,24)/t13-,15-,18-,19-,20+/m1/s1
SMILES:	O=C1C[C@@H]2[C@](C3=C1[C@@H](O)[C@@](O)(CC3)C(O)(C)C)(C)CCC[C@@]2(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333393
PubChem CID:	71578632
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO33033	chinese eaglewood	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23394318]

☑ 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
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1072	Individual Protein	Serotonin transporter	Rattus norvegicus	Inhibition	=	52.7	%	PMID[491673]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[491673]

☑ 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 NPC198880 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1442
0.2-0.3	5042
0.3-0.4	9603
0.4-0.5	12887
0.5-0.6	7379
0.6-0.7	4984
0.7-0.8	1075
0.8-0.85	54
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8557	High Similarity	NPC37646
0.8515	High Similarity	NPC251017
0.8469	Intermediate Similarity	NPC40765
0.8469	Intermediate Similarity	NPC243525
0.8469	Intermediate Similarity	NPC3772
0.8438	Intermediate Similarity	NPC73457
0.8416	Intermediate Similarity	NPC80781
0.84	Intermediate Similarity	NPC316964
0.8384	Intermediate Similarity	NPC122294
0.8384	Intermediate Similarity	NPC106557
0.8384	Intermediate Similarity	NPC121339
0.837	Intermediate Similarity	NPC66764
0.837	Intermediate Similarity	NPC110150
0.8367	Intermediate Similarity	NPC255809
0.8351	Intermediate Similarity	NPC131840
0.835	Intermediate Similarity	NPC51452
0.835	Intermediate Similarity	NPC323834
0.8316	Intermediate Similarity	NPC476796
0.8302	Intermediate Similarity	NPC472928
0.83	Intermediate Similarity	NPC16021
0.8269	Intermediate Similarity	NPC473037
0.8265	Intermediate Similarity	NPC472976
0.8265	Intermediate Similarity	NPC196227
0.8265	Intermediate Similarity	NPC472977
0.8247	Intermediate Similarity	NPC116726
0.8218	Intermediate Similarity	NPC51370
0.8218	Intermediate Similarity	NPC144660
0.8218	Intermediate Similarity	NPC287833
0.8218	Intermediate Similarity	NPC88198
0.8218	Intermediate Similarity	NPC299971
0.8218	Intermediate Similarity	NPC157787
0.8218	Intermediate Similarity	NPC307954
0.8211	Intermediate Similarity	NPC220930
0.8211	Intermediate Similarity	NPC272039
0.8208	Intermediate Similarity	NPC473036
0.8208	Intermediate Similarity	NPC286880
0.8208	Intermediate Similarity	NPC272898
0.819	Intermediate Similarity	NPC295244
0.8182	Intermediate Similarity	NPC173875
0.8182	Intermediate Similarity	NPC469995
0.8182	Intermediate Similarity	NPC318282
0.8182	Intermediate Similarity	NPC53565
0.8182	Intermediate Similarity	NPC174948
0.8163	Intermediate Similarity	NPC477435
0.8163	Intermediate Similarity	NPC477436
0.8155	Intermediate Similarity	NPC475050
0.8155	Intermediate Similarity	NPC55872
0.8155	Intermediate Similarity	NPC159533
0.8144	Intermediate Similarity	NPC134321
0.8137	Intermediate Similarity	NPC302537
0.8137	Intermediate Similarity	NPC163372
0.8119	Intermediate Similarity	NPC478056
0.8119	Intermediate Similarity	NPC10364
0.8113	Intermediate Similarity	NPC286174
0.8113	Intermediate Similarity	NPC77947
0.8108	Intermediate Similarity	NPC268958
0.8108	Intermediate Similarity	NPC472933
0.81	Intermediate Similarity	NPC328371
0.81	Intermediate Similarity	NPC95565
0.81	Intermediate Similarity	NPC476797
0.81	Intermediate Similarity	NPC117133
0.8095	Intermediate Similarity	NPC9457
0.8095	Intermediate Similarity	NPC471783
0.8095	Intermediate Similarity	NPC112780
0.8095	Intermediate Similarity	NPC472925
0.8091	Intermediate Similarity	NPC472934
0.8081	Intermediate Similarity	NPC470957
0.8081	Intermediate Similarity	NPC166906
0.8081	Intermediate Similarity	NPC184870
0.8081	Intermediate Similarity	NPC470958
0.8077	Intermediate Similarity	NPC28656
0.8073	Intermediate Similarity	NPC284915
0.8061	Intermediate Similarity	NPC107690
0.8061	Intermediate Similarity	NPC235704
0.8061	Intermediate Similarity	NPC472978
0.8058	Intermediate Similarity	NPC293753
0.8058	Intermediate Similarity	NPC281702
0.8058	Intermediate Similarity	NPC473424
0.8058	Intermediate Similarity	NPC295791
0.8058	Intermediate Similarity	NPC234892
0.8058	Intermediate Similarity	NPC308726
0.8058	Intermediate Similarity	NPC119601
0.8056	Intermediate Similarity	NPC472002
0.8056	Intermediate Similarity	NPC269530
0.8056	Intermediate Similarity	NPC285956
0.8039	Intermediate Similarity	NPC205899
0.8037	Intermediate Similarity	NPC129689
0.802	Intermediate Similarity	NPC320306
0.802	Intermediate Similarity	NPC43747
0.802	Intermediate Similarity	NPC18319
0.8019	Intermediate Similarity	NPC65941
0.8018	Intermediate Similarity	NPC251310
0.8	Intermediate Similarity	NPC181357
0.8	Intermediate Similarity	NPC317586
0.8	Intermediate Similarity	NPC241156
0.8	Intermediate Similarity	NPC297199
0.8	Intermediate Similarity	NPC477437
0.8	Intermediate Similarity	NPC477438
0.8	Intermediate Similarity	NPC473170
0.8	Intermediate Similarity	NPC270929
0.8	Intermediate Similarity	NPC200702
0.8	Intermediate Similarity	NPC470016
0.8	Intermediate Similarity	NPC64318
0.7982	Intermediate Similarity	NPC472929
0.7981	Intermediate Similarity	NPC90177
0.7981	Intermediate Similarity	NPC33973
0.7981	Intermediate Similarity	NPC70967
0.798	Intermediate Similarity	NPC271652
0.798	Intermediate Similarity	NPC470254
0.7963	Intermediate Similarity	NPC115303
0.7963	Intermediate Similarity	NPC188738
0.7961	Intermediate Similarity	NPC115862
0.7961	Intermediate Similarity	NPC470184
0.7961	Intermediate Similarity	NPC472924
0.7961	Intermediate Similarity	NPC81530
0.7959	Intermediate Similarity	NPC230332
0.7959	Intermediate Similarity	NPC128672
0.7941	Intermediate Similarity	NPC174663
0.7941	Intermediate Similarity	NPC471717
0.7938	Intermediate Similarity	NPC48107
0.7928	Intermediate Similarity	NPC472927
0.7928	Intermediate Similarity	NPC55296
0.7925	Intermediate Similarity	NPC473284
0.7925	Intermediate Similarity	NPC473165
0.7921	Intermediate Similarity	NPC472806
0.7921	Intermediate Similarity	NPC167193
0.7921	Intermediate Similarity	NPC328162
0.7921	Intermediate Similarity	NPC7124
0.7921	Intermediate Similarity	NPC305483
0.7921	Intermediate Similarity	NPC472941
0.7921	Intermediate Similarity	NPC456
0.7921	Intermediate Similarity	NPC125622
0.7921	Intermediate Similarity	NPC249954
0.7921	Intermediate Similarity	NPC96859
0.7917	Intermediate Similarity	NPC475181
0.7917	Intermediate Similarity	NPC472974
0.7917	Intermediate Similarity	NPC473226
0.7917	Intermediate Similarity	NPC229717
0.7909	Intermediate Similarity	NPC67259
0.7909	Intermediate Similarity	NPC147912
0.7909	Intermediate Similarity	NPC117712
0.7905	Intermediate Similarity	NPC2436
0.7905	Intermediate Similarity	NPC216245
0.7905	Intermediate Similarity	NPC284865
0.7905	Intermediate Similarity	NPC65523
0.7905	Intermediate Similarity	NPC135854
0.7905	Intermediate Similarity	NPC470251
0.79	Intermediate Similarity	NPC477439
0.79	Intermediate Similarity	NPC240617
0.7885	Intermediate Similarity	NPC56498
0.7885	Intermediate Similarity	NPC477915
0.7885	Intermediate Similarity	NPC204450
0.7885	Intermediate Similarity	NPC136289
0.7885	Intermediate Similarity	NPC195290
0.7879	Intermediate Similarity	NPC63748
0.787	Intermediate Similarity	NPC470496
0.7864	Intermediate Similarity	NPC35239
0.7864	Intermediate Similarity	NPC327431
0.7864	Intermediate Similarity	NPC474012
0.7864	Intermediate Similarity	NPC117685
0.7864	Intermediate Similarity	NPC476299
0.7857	Intermediate Similarity	NPC329736
0.7857	Intermediate Similarity	NPC186525
0.7857	Intermediate Similarity	NPC472489
0.7857	Intermediate Similarity	NPC472973
0.785	Intermediate Similarity	NPC151393
0.7843	Intermediate Similarity	NPC89225
0.7843	Intermediate Similarity	NPC170131
0.7835	Intermediate Similarity	NPC99909
0.783	Intermediate Similarity	NPC470587
0.783	Intermediate Similarity	NPC149047
0.783	Intermediate Similarity	NPC1679
0.7822	Intermediate Similarity	NPC134067
0.7822	Intermediate Similarity	NPC148523
0.7822	Intermediate Similarity	NPC259286
0.7822	Intermediate Similarity	NPC266899
0.7818	Intermediate Similarity	NPC471204
0.781	Intermediate Similarity	NPC275583
0.781	Intermediate Similarity	NPC236390
0.781	Intermediate Similarity	NPC95899
0.781	Intermediate Similarity	NPC478057
0.781	Intermediate Similarity	NPC159442
0.781	Intermediate Similarity	NPC264048
0.78	Intermediate Similarity	NPC25750
0.78	Intermediate Similarity	NPC472930
0.78	Intermediate Similarity	NPC69454
0.7798	Intermediate Similarity	NPC171888
0.7798	Intermediate Similarity	NPC146945
0.7789	Intermediate Similarity	NPC64600
0.7789	Intermediate Similarity	NPC251475
0.7789	Intermediate Similarity	NPC169941
0.7788	Intermediate Similarity	NPC61520
0.7788	Intermediate Similarity	NPC282524
0.7788	Intermediate Similarity	NPC97435
0.7788	Intermediate Similarity	NPC469327
0.7788	Intermediate Similarity	NPC124211
0.7788	Intermediate Similarity	NPC230513
0.7778	Intermediate Similarity	NPC214644
0.7778	Intermediate Similarity	NPC472307
0.7778	Intermediate Similarity	NPC220705

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 NPC198880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1955
0.2-0.3	3722
0.3-0.4	2105
0.4-0.5	697
0.5-0.6	266
0.6-0.7	187
0.7-0.8	7
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
0.7768	Intermediate Similarity	NPD7115	Discovery
0.7596	Intermediate Similarity	NPD4225	Approved
0.7525	Intermediate Similarity	NPD7515	Phase 2
0.7383	Intermediate Similarity	NPD5211	Phase 2
0.7374	Intermediate Similarity	NPD3618	Phase 1
0.7353	Intermediate Similarity	NPD6411	Approved
0.7339	Intermediate Similarity	NPD6402	Approved
0.7339	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD6675	Approved
0.7339	Intermediate Similarity	NPD7128	Approved
0.7333	Intermediate Similarity	NPD4755	Approved
0.7327	Intermediate Similarity	NPD5328	Approved
0.7297	Intermediate Similarity	NPD6372	Approved
0.7297	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6373	Approved
0.7282	Intermediate Similarity	NPD5779	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7273	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD5701	Approved
0.7248	Intermediate Similarity	NPD5141	Approved
0.7238	Intermediate Similarity	NPD4697	Phase 3
0.7232	Intermediate Similarity	NPD4634	Approved
0.7212	Intermediate Similarity	NPD7748	Approved
0.7207	Intermediate Similarity	NPD6881	Approved
0.7207	Intermediate Similarity	NPD7320	Approved
0.7207	Intermediate Similarity	NPD6899	Approved
0.72	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5286	Approved
0.7196	Intermediate Similarity	NPD5285	Approved
0.7196	Intermediate Similarity	NPD4700	Approved
0.7196	Intermediate Similarity	NPD4696	Approved
0.7184	Intermediate Similarity	NPD6079	Approved
0.717	Intermediate Similarity	NPD7902	Approved
0.7168	Intermediate Similarity	NPD6650	Approved
0.7168	Intermediate Similarity	NPD6649	Approved
0.7157	Intermediate Similarity	NPD6101	Approved
0.7157	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7119	Intermediate Similarity	NPD6319	Approved
0.7105	Intermediate Similarity	NPD8297	Approved
0.7103	Intermediate Similarity	NPD5696	Approved
0.708	Intermediate Similarity	NPD6883	Approved
0.708	Intermediate Similarity	NPD7102	Approved
0.708	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7290	Approved
0.7075	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5221	Approved
0.7075	Intermediate Similarity	NPD5222	Approved
0.7064	Intermediate Similarity	NPD5225	Approved
0.7064	Intermediate Similarity	NPD5226	Approved
0.7064	Intermediate Similarity	NPD5224	Approved
0.7064	Intermediate Similarity	NPD4633	Approved
0.7054	Intermediate Similarity	NPD6011	Approved
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4632	Approved
0.7018	Intermediate Similarity	NPD8130	Phase 1
0.7018	Intermediate Similarity	NPD6869	Approved
0.7018	Intermediate Similarity	NPD6847	Approved
0.7018	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD5175	Approved
0.7	Intermediate Similarity	NPD5174	Approved
0.6991	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5210	Approved
0.6981	Remote Similarity	NPD4629	Approved
0.6981	Remote Similarity	NPD5695	Phase 3
0.6972	Remote Similarity	NPD5223	Approved
0.697	Remote Similarity	NPD3667	Approved
0.6961	Remote Similarity	NPD3573	Approved
0.6957	Remote Similarity	NPD6882	Approved
0.6952	Remote Similarity	NPD6399	Phase 3
0.6952	Remote Similarity	NPD4202	Approved
0.6942	Remote Similarity	NPD8328	Phase 3
0.6887	Remote Similarity	NPD7900	Approved
0.6887	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7640	Approved
0.6881	Remote Similarity	NPD7639	Approved
0.6875	Remote Similarity	NPD4767	Approved
0.6875	Remote Similarity	NPD4768	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.687	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5284	Approved
0.6857	Remote Similarity	NPD5281	Approved
0.6852	Remote Similarity	NPD6083	Phase 2
0.6852	Remote Similarity	NPD6084	Phase 2
0.6847	Remote Similarity	NPD4754	Approved
0.6832	Remote Similarity	NPD3666	Approved
0.6832	Remote Similarity	NPD4786	Approved
0.6832	Remote Similarity	NPD3133	Approved
0.6832	Remote Similarity	NPD3665	Phase 1
0.6827	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4753	Phase 2
0.6814	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7638	Approved
0.678	Remote Similarity	NPD6274	Approved
0.6765	Remote Similarity	NPD1694	Approved
0.6759	Remote Similarity	NPD7614	Phase 1
0.6757	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD4730	Approved
0.6754	Remote Similarity	NPD4729	Approved
0.6754	Remote Similarity	NPD5128	Approved
0.6748	Remote Similarity	NPD7492	Approved
0.6723	Remote Similarity	NPD6009	Approved
0.6699	Remote Similarity	NPD4519	Discontinued
0.6699	Remote Similarity	NPD4623	Approved
0.6699	Remote Similarity	NPD5279	Phase 3
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD6059	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7319	Approved
0.664	Remote Similarity	NPD8293	Discontinued
0.664	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6638	Remote Similarity	NPD5247	Approved
0.6638	Remote Similarity	NPD5250	Approved
0.6638	Remote Similarity	NPD5248	Approved
0.6638	Remote Similarity	NPD5251	Approved
0.6638	Remote Similarity	NPD5249	Phase 3
0.6612	Remote Similarity	NPD7100	Approved
0.6612	Remote Similarity	NPD7101	Approved
0.6604	Remote Similarity	NPD5785	Approved
0.6602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1696	Phase 3
0.6602	Remote Similarity	NPD5363	Approved
0.66	Remote Similarity	NPD4695	Discontinued
0.6587	Remote Similarity	NPD7736	Approved
0.6585	Remote Similarity	NPD6370	Approved
0.6585	Remote Similarity	NPD5988	Approved
0.6583	Remote Similarity	NPD6317	Approved
0.6581	Remote Similarity	NPD5217	Approved
0.6581	Remote Similarity	NPD5215	Approved
0.6581	Remote Similarity	NPD5216	Approved
0.6566	Remote Similarity	NPD3617	Approved
0.656	Remote Similarity	NPD7507	Approved
0.6538	Remote Similarity	NPD5330	Approved
0.6538	Remote Similarity	NPD7521	Approved
0.6538	Remote Similarity	NPD6684	Approved
0.6538	Remote Similarity	NPD7334	Approved
0.6538	Remote Similarity	NPD6409	Approved
0.6538	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD5786	Approved
0.6529	Remote Similarity	NPD6314	Approved
0.6529	Remote Similarity	NPD6313	Approved
0.6529	Remote Similarity	NPD6335	Approved
0.6514	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3668	Phase 3
0.6504	Remote Similarity	NPD8513	Phase 3
0.6504	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6908	Approved
0.6504	Remote Similarity	NPD8516	Approved
0.6504	Remote Similarity	NPD5983	Phase 2
0.6504	Remote Similarity	NPD8517	Approved
0.6504	Remote Similarity	NPD6909	Approved
0.6504	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD6868	Approved
0.6496	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6371	Approved
0.6496	Remote Similarity	NPD5135	Approved
0.6496	Remote Similarity	NPD5169	Approved
0.6471	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4270	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6471	Remote Similarity	NPD4269	Approved
0.6466	Remote Similarity	NPD6686	Approved
0.6466	Remote Similarity	NPD5168	Approved
0.6455	Remote Similarity	NPD7732	Phase 3
0.6441	Remote Similarity	NPD5127	Approved
0.6415	Remote Similarity	NPD6903	Approved
0.6415	Remote Similarity	NPD5737	Approved
0.6415	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6672	Approved
0.64	Remote Similarity	NPD7604	Phase 2
0.6389	Remote Similarity	NPD7983	Approved
0.6389	Remote Similarity	NPD8034	Phase 2
0.6389	Remote Similarity	NPD8035	Phase 2
0.6387	Remote Similarity	NPD6053	Discontinued
0.6381	Remote Similarity	NPD4694	Approved
0.6381	Remote Similarity	NPD5690	Phase 2
0.6381	Remote Similarity	NPD5280	Approved
0.6379	Remote Similarity	NPD6412	Phase 2
0.6373	Remote Similarity	NPD4139	Approved
0.6373	Remote Similarity	NPD4692	Approved
0.6371	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD6117	Approved
0.6346	Remote Similarity	NPD4197	Approved
0.6344	Remote Similarity	NPD7341	Phase 2
0.6311	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7260	Phase 2
0.63	Remote Similarity	NPD6116	Phase 1
0.6299	Remote Similarity	NPD6336	Discontinued
0.6296	Remote Similarity	NPD5692	Phase 3
0.6296	Remote Similarity	NPD5207	Approved
0.6286	Remote Similarity	NPD5329	Approved
0.6281	Remote Similarity	NPD5167	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