NPASS Compound

Structure

NPC472825 OpenBabel07101718312D 28 31 0 0 1 0 0 0 0 0999 V2000 -5.8310 4.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5412 -0.0675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8160 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 2.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8032 0.9137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0238 -0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1743 0.5631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3198 1.6711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5262 -0.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2108 3.0030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1958 2.0031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5669 1.6524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8140 1.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9272 0.5817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0842 3.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5561 0.9324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 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 0.3601 -1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6874 2.1207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0991 4.4899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2667 -1.4279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9426 2.9771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 28 1 0 0 0 0 4 8 1 0 0 0 0 4 15 1 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 19 1 1 0 0 0 16 24 2 0 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 2 1 1 0 0 0 20 8 1 1 0 0 0 21 22 1 1 0 0 0 21 26 1 0 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	397.038
LogP:	1.334
LogD:	1.24
LogS:	-3.408
# Rotatable Bonds:	4
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	6.168
Fsp3:	0.727
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:	-5.538
MDCK Permeability:	1.5505966075579636e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.11
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.734

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	89.29109191894531%
Volume Distribution (VD):	0.908
Pgp-substrate:	10.985623359680176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.682
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.384
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.464

ADMET: Excretion

Clearance (CL):	3.12
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.707
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.316
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.764
Carcinogencity:	0.95
Eye Corrosion:	0.004
Eye Irritation:	0.023
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: NPC472825

Natural Product ID:	NPC472825
*Common Name:**	USIWAMBUPSEYIB-XJLRFKRQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	USIWAMBUPSEYIB-XJLRFKRQSA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-3-28-18(25)10-14-15-4-8-20-11-21(26,22(27,12-20)13-23)9-6-17(20)19(15,2)7-5-16(14)24/h5,7,10,15,17,23,26-27H,3-4,6,8-9,11-13H2,1-2H3/b14-10-/t15-,17+,19-,20+,21-,22+/m1/s1
SMILES:	CCOC(=O)C=C1C2CCC34CC(CCC3C2(C=CC1=O)C)(C(C4)(CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586292
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO32576	tricalysia fruticosa	Species	Rubiaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[26052978]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	6600.0	nM	PMID[532511]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	>	90.0	%	PMID[532511]

☑ 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 NPC472825 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	199
0.1-0.2	1128
0.2-0.3	3879
0.3-0.4	7666
0.4-0.5	13375
0.5-0.6	6050
0.6-0.7	6767
0.7-0.8	3284
0.8-0.85	317
0.85-0.9	30
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC472824
0.8661	High Similarity	NPC79579
0.8649	High Similarity	NPC257457
0.8649	High Similarity	NPC311554
0.8636	High Similarity	NPC148458
0.8598	High Similarity	NPC173905
0.8598	High Similarity	NPC5475
0.8598	High Similarity	NPC284828
0.8598	High Similarity	NPC472216
0.8596	High Similarity	NPC473979
0.8571	High Similarity	NPC472819
0.8571	High Similarity	NPC264954
0.8559	High Similarity	NPC239273
0.8558	High Similarity	NPC22388
0.8545	High Similarity	NPC147912
0.8545	High Similarity	NPC67259
0.8532	High Similarity	NPC191620
0.8532	High Similarity	NPC100267
0.8532	High Similarity	NPC475524
0.8522	High Similarity	NPC8374
0.8496	Intermediate Similarity	NPC474370
0.8491	Intermediate Similarity	NPC472818
0.8482	Intermediate Similarity	NPC153440
0.8476	Intermediate Similarity	NPC112009
0.8468	Intermediate Similarity	NPC190286
0.8455	Intermediate Similarity	NPC962
0.8455	Intermediate Similarity	NPC250109
0.8426	Intermediate Similarity	NPC10064
0.8426	Intermediate Similarity	NPC170221
0.8421	Intermediate Similarity	NPC46570
0.8421	Intermediate Similarity	NPC67569
0.8411	Intermediate Similarity	NPC44063
0.8411	Intermediate Similarity	NPC472820
0.8411	Intermediate Similarity	NPC475294
0.8407	Intermediate Similarity	NPC475041
0.8407	Intermediate Similarity	NPC5292
0.8396	Intermediate Similarity	NPC472822
0.8393	Intermediate Similarity	NPC167606
0.8393	Intermediate Similarity	NPC286528
0.8393	Intermediate Similarity	NPC20302
0.8393	Intermediate Similarity	NPC470492
0.8393	Intermediate Similarity	NPC140055
0.8393	Intermediate Similarity	NPC471854
0.8364	Intermediate Similarity	NPC470063
0.8364	Intermediate Similarity	NPC236217
0.835	Intermediate Similarity	NPC108078
0.835	Intermediate Similarity	NPC231751
0.835	Intermediate Similarity	NPC253826
0.8349	Intermediate Similarity	NPC179642
0.8349	Intermediate Similarity	NPC6206
0.8348	Intermediate Similarity	NPC88326
0.8348	Intermediate Similarity	NPC107493
0.8348	Intermediate Similarity	NPC153700
0.8348	Intermediate Similarity	NPC470265
0.8348	Intermediate Similarity	NPC23786
0.8333	Intermediate Similarity	NPC476961
0.8333	Intermediate Similarity	NPC472219
0.8333	Intermediate Similarity	NPC474585
0.8333	Intermediate Similarity	NPC472217
0.8333	Intermediate Similarity	NPC472218
0.8319	Intermediate Similarity	NPC709
0.8319	Intermediate Similarity	NPC50774
0.8319	Intermediate Similarity	NPC146786
0.8318	Intermediate Similarity	NPC186668
0.8318	Intermediate Similarity	NPC266570
0.8304	Intermediate Similarity	NPC49492
0.8304	Intermediate Similarity	NPC196931
0.8304	Intermediate Similarity	NPC266728
0.8302	Intermediate Similarity	NPC472821
0.8302	Intermediate Similarity	NPC180204
0.8288	Intermediate Similarity	NPC122056
0.8276	Intermediate Similarity	NPC469789
0.8276	Intermediate Similarity	NPC11895
0.8273	Intermediate Similarity	NPC474315
0.8273	Intermediate Similarity	NPC470961
0.8269	Intermediate Similarity	NPC114274
0.8269	Intermediate Similarity	NPC108368
0.8269	Intermediate Similarity	NPC57079
0.8257	Intermediate Similarity	NPC2766
0.8257	Intermediate Similarity	NPC475065
0.8252	Intermediate Similarity	NPC234993
0.8252	Intermediate Similarity	NPC134072
0.8246	Intermediate Similarity	NPC473270
0.8246	Intermediate Similarity	NPC270850
0.8246	Intermediate Similarity	NPC305260
0.8241	Intermediate Similarity	NPC330011
0.8241	Intermediate Similarity	NPC329048
0.8241	Intermediate Similarity	NPC477916
0.8241	Intermediate Similarity	NPC83744
0.8235	Intermediate Similarity	NPC471407
0.8235	Intermediate Similarity	NPC231529
0.823	Intermediate Similarity	NPC183580
0.823	Intermediate Similarity	NPC312824
0.823	Intermediate Similarity	NPC284068
0.823	Intermediate Similarity	NPC476965
0.823	Intermediate Similarity	NPC470493
0.823	Intermediate Similarity	NPC470959
0.8224	Intermediate Similarity	NPC204833
0.8224	Intermediate Similarity	NPC255309
0.8224	Intermediate Similarity	NPC209502
0.8224	Intermediate Similarity	NPC472868
0.8214	Intermediate Similarity	NPC470953
0.8208	Intermediate Similarity	NPC155332
0.8208	Intermediate Similarity	NPC32577
0.8208	Intermediate Similarity	NPC114540
0.8205	Intermediate Similarity	NPC8369
0.8205	Intermediate Similarity	NPC172154
0.8205	Intermediate Similarity	NPC81736
0.82	Intermediate Similarity	NPC5509
0.82	Intermediate Similarity	NPC476733
0.82	Intermediate Similarity	NPC215029
0.8198	Intermediate Similarity	NPC221144
0.8198	Intermediate Similarity	NPC207251
0.819	Intermediate Similarity	NPC170538
0.819	Intermediate Similarity	NPC154072
0.819	Intermediate Similarity	NPC472826
0.819	Intermediate Similarity	NPC167974
0.819	Intermediate Similarity	NPC269642
0.819	Intermediate Similarity	NPC251680
0.819	Intermediate Similarity	NPC201406
0.8182	Intermediate Similarity	NPC16270
0.8182	Intermediate Similarity	NPC37116
0.8182	Intermediate Similarity	NPC197428
0.8182	Intermediate Similarity	NPC29133
0.8182	Intermediate Similarity	NPC5284
0.8182	Intermediate Similarity	NPC41551
0.8182	Intermediate Similarity	NPC76084
0.8182	Intermediate Similarity	NPC235077
0.8174	Intermediate Similarity	NPC41123
0.8174	Intermediate Similarity	NPC145074
0.8174	Intermediate Similarity	NPC476962
0.8174	Intermediate Similarity	NPC114939
0.8173	Intermediate Similarity	NPC57416
0.8173	Intermediate Similarity	NPC107243
0.8165	Intermediate Similarity	NPC473482
0.8165	Intermediate Similarity	NPC177064
0.8165	Intermediate Similarity	NPC329417
0.8165	Intermediate Similarity	NPC475418
0.8165	Intermediate Similarity	NPC318363
0.8158	Intermediate Similarity	NPC329736
0.8155	Intermediate Similarity	NPC171395
0.8148	Intermediate Similarity	NPC171137
0.8148	Intermediate Similarity	NPC152695
0.8148	Intermediate Similarity	NPC202167
0.8148	Intermediate Similarity	NPC149047
0.8148	Intermediate Similarity	NPC85829
0.8148	Intermediate Similarity	NPC189863
0.8148	Intermediate Similarity	NPC319077
0.8148	Intermediate Similarity	NPC302607
0.8148	Intermediate Similarity	NPC97202
0.8148	Intermediate Similarity	NPC257353
0.8148	Intermediate Similarity	NPC49958
0.8148	Intermediate Similarity	NPC260268
0.8148	Intermediate Similarity	NPC96377
0.8148	Intermediate Similarity	NPC214264
0.8148	Intermediate Similarity	NPC60681
0.8148	Intermediate Similarity	NPC150531
0.8148	Intermediate Similarity	NPC296945
0.8148	Intermediate Similarity	NPC50692
0.8148	Intermediate Similarity	NPC476027
0.8148	Intermediate Similarity	NPC48733
0.8142	Intermediate Similarity	NPC469794
0.8142	Intermediate Similarity	NPC64318
0.8142	Intermediate Similarity	NPC176840
0.8142	Intermediate Similarity	NPC72772
0.8137	Intermediate Similarity	NPC139692
0.8136	Intermediate Similarity	NPC293112
0.8136	Intermediate Similarity	NPC159499
0.8136	Intermediate Similarity	NPC15095
0.8131	Intermediate Similarity	NPC478057
0.8131	Intermediate Similarity	NPC187302
0.8131	Intermediate Similarity	NPC196471
0.8131	Intermediate Similarity	NPC36688
0.8131	Intermediate Similarity	NPC189588
0.8131	Intermediate Similarity	NPC97487
0.8131	Intermediate Similarity	NPC10232
0.8125	Intermediate Similarity	NPC194100
0.8125	Intermediate Similarity	NPC178981
0.8125	Intermediate Similarity	NPC317210
0.812	Intermediate Similarity	NPC204812
0.8113	Intermediate Similarity	NPC224720
0.8113	Intermediate Similarity	NPC475099
0.8113	Intermediate Similarity	NPC476240
0.8113	Intermediate Similarity	NPC268829
0.8113	Intermediate Similarity	NPC476223
0.8113	Intermediate Similarity	NPC247701
0.8113	Intermediate Similarity	NPC471412
0.8113	Intermediate Similarity	NPC25177
0.8113	Intermediate Similarity	NPC295110
0.8113	Intermediate Similarity	NPC222875
0.8108	Intermediate Similarity	NPC470076
0.8103	Intermediate Similarity	NPC470878
0.8103	Intermediate Similarity	NPC473256
0.8099	Intermediate Similarity	NPC471855
0.8095	Intermediate Similarity	NPC181147
0.8095	Intermediate Similarity	NPC98868
0.8095	Intermediate Similarity	NPC477854
0.8091	Intermediate Similarity	NPC214644
0.8087	Intermediate Similarity	NPC61520
0.8087	Intermediate Similarity	NPC476960

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 NPC472825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1310
0.2-0.3	3622
0.3-0.4	2624
0.4-0.5	882
0.5-0.6	200
0.6-0.7	152
0.7-0.8	148
0.8-0.85	42
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8411	Intermediate Similarity	NPD5697	Approved
0.8393	Intermediate Similarity	NPD7115	Discovery
0.835	Intermediate Similarity	NPD6083	Phase 2
0.835	Intermediate Similarity	NPD6084	Phase 2
0.8333	Intermediate Similarity	NPD6319	Approved
0.8333	Intermediate Similarity	NPD6881	Approved
0.8333	Intermediate Similarity	NPD6899	Approved
0.8288	Intermediate Similarity	NPD4632	Approved
0.8269	Intermediate Similarity	NPD7638	Approved
0.8257	Intermediate Similarity	NPD6014	Approved
0.8257	Intermediate Similarity	NPD6012	Approved
0.8257	Intermediate Similarity	NPD6013	Approved
0.8198	Intermediate Similarity	NPD8297	Approved
0.819	Intermediate Similarity	NPD7640	Approved
0.819	Intermediate Similarity	NPD7639	Approved
0.8182	Intermediate Similarity	NPD7102	Approved
0.8182	Intermediate Similarity	NPD6883	Approved
0.8182	Intermediate Similarity	NPD4634	Approved
0.8182	Intermediate Similarity	NPD7290	Approved
0.8165	Intermediate Similarity	NPD6011	Approved
0.8155	Intermediate Similarity	NPD5695	Phase 3
0.8148	Intermediate Similarity	NPD6675	Approved
0.8148	Intermediate Similarity	NPD7128	Approved
0.8148	Intermediate Similarity	NPD6402	Approved
0.8148	Intermediate Similarity	NPD5739	Approved
0.8108	Intermediate Similarity	NPD6649	Approved
0.8108	Intermediate Similarity	NPD6847	Approved
0.8108	Intermediate Similarity	NPD8130	Phase 1
0.8108	Intermediate Similarity	NPD6869	Approved
0.8108	Intermediate Similarity	NPD6650	Approved
0.8108	Intermediate Similarity	NPD6617	Approved
0.8095	Intermediate Similarity	NPD5696	Approved
0.8073	Intermediate Similarity	NPD5701	Approved
0.8039	Intermediate Similarity	NPD5693	Phase 1
0.8037	Intermediate Similarity	NPD5211	Phase 2
0.8036	Intermediate Similarity	NPD6882	Approved
0.802	Intermediate Similarity	NPD4753	Phase 2
0.8019	Intermediate Similarity	NPD5286	Approved
0.8019	Intermediate Similarity	NPD5285	Approved
0.8019	Intermediate Similarity	NPD4696	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.7981	Intermediate Similarity	NPD5210	Approved
0.7981	Intermediate Similarity	NPD4629	Approved
0.7928	Intermediate Similarity	NPD6372	Approved
0.7928	Intermediate Similarity	NPD6373	Approved
0.7913	Intermediate Similarity	NPD6009	Approved
0.7899	Intermediate Similarity	NPD7492	Approved
0.789	Intermediate Similarity	NPD5141	Approved
0.787	Intermediate Similarity	NPD5225	Approved
0.787	Intermediate Similarity	NPD5226	Approved
0.787	Intermediate Similarity	NPD5224	Approved
0.787	Intermediate Similarity	NPD4633	Approved
0.7863	Intermediate Similarity	NPD6054	Approved
0.7833	Intermediate Similarity	NPD7507	Approved
0.7833	Intermediate Similarity	NPD6616	Approved
0.783	Intermediate Similarity	NPD4755	Approved
0.7798	Intermediate Similarity	NPD5174	Approved
0.7798	Intermediate Similarity	NPD5175	Approved
0.7797	Intermediate Similarity	NPD6016	Approved
0.7797	Intermediate Similarity	NPD5983	Phase 2
0.7797	Intermediate Similarity	NPD6015	Approved
0.7788	Intermediate Similarity	NPD4202	Approved
0.7778	Intermediate Similarity	NPD5223	Approved
0.7769	Intermediate Similarity	NPD7078	Approved
0.7768	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6412	Phase 2
0.7731	Intermediate Similarity	NPD6370	Approved
0.7731	Intermediate Similarity	NPD5988	Approved
0.7723	Intermediate Similarity	NPD5330	Approved
0.7723	Intermediate Similarity	NPD7146	Approved
0.7723	Intermediate Similarity	NPD6684	Approved
0.7723	Intermediate Similarity	NPD7521	Approved
0.7723	Intermediate Similarity	NPD7334	Approved
0.7723	Intermediate Similarity	NPD6409	Approved
0.7705	Intermediate Similarity	NPD7736	Approved
0.77	Intermediate Similarity	NPD3665	Phase 1
0.77	Intermediate Similarity	NPD3133	Approved
0.77	Intermediate Similarity	NPD3666	Approved
0.7692	Intermediate Similarity	NPD6079	Approved
0.7692	Intermediate Similarity	NPD5281	Approved
0.7692	Intermediate Similarity	NPD5284	Approved
0.7685	Intermediate Similarity	NPD4700	Approved
0.7679	Intermediate Similarity	NPD6686	Approved
0.7677	Intermediate Similarity	NPD4223	Phase 3
0.7677	Intermediate Similarity	NPD4221	Approved
0.7672	Intermediate Similarity	NPD6274	Approved
0.767	Intermediate Similarity	NPD6080	Approved
0.767	Intermediate Similarity	NPD6904	Approved
0.767	Intermediate Similarity	NPD6673	Approved
0.7667	Intermediate Similarity	NPD7604	Phase 2
0.7658	Intermediate Similarity	NPD6008	Approved
0.7647	Intermediate Similarity	NPD7503	Approved
0.7642	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7319	Approved
0.7632	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7100	Approved
0.7627	Intermediate Similarity	NPD7101	Approved
0.7619	Intermediate Similarity	NPD6399	Phase 3
0.7607	Intermediate Similarity	NPD6317	Approved
0.7593	Intermediate Similarity	NPD4225	Approved
0.7573	Intermediate Similarity	NPD5208	Approved
0.7573	Intermediate Similarity	NPD5737	Approved
0.7573	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD6672	Approved
0.7573	Intermediate Similarity	NPD6903	Approved
0.757	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5222	Approved
0.757	Intermediate Similarity	NPD5221	Approved
0.7565	Intermediate Similarity	NPD6053	Discontinued
0.7563	Intermediate Similarity	NPD6059	Approved
0.7549	Intermediate Similarity	NPD5690	Phase 2
0.7549	Intermediate Similarity	NPD3618	Phase 1
0.7545	Intermediate Similarity	NPD7632	Discontinued
0.7542	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD6314	Approved
0.7542	Intermediate Similarity	NPD6335	Approved
0.7542	Intermediate Similarity	NPD6313	Approved
0.7542	Intermediate Similarity	NPD7328	Approved
0.7541	Intermediate Similarity	NPD6336	Discontinued
0.7525	Intermediate Similarity	NPD4197	Approved
0.7524	Intermediate Similarity	NPD5694	Approved
0.7522	Intermediate Similarity	NPD4730	Approved
0.7522	Intermediate Similarity	NPD4729	Approved
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7479	Intermediate Similarity	NPD7516	Approved
0.7451	Intermediate Similarity	NPD5329	Approved
0.7429	Intermediate Similarity	NPD5207	Approved
0.7429	Intermediate Similarity	NPD5692	Phase 3
0.7417	Intermediate Similarity	NPD8377	Approved
0.7417	Intermediate Similarity	NPD8294	Approved
0.7391	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5250	Approved
0.7391	Intermediate Similarity	NPD5248	Approved
0.7391	Intermediate Similarity	NPD5247	Approved
0.7391	Intermediate Similarity	NPD5249	Phase 3
0.7391	Intermediate Similarity	NPD5251	Approved
0.7383	Intermediate Similarity	NPD7748	Approved
0.7383	Intermediate Similarity	NPD6001	Approved
0.7379	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6098	Approved
0.7379	Intermediate Similarity	NPD4690	Approved
0.7379	Intermediate Similarity	NPD4693	Phase 3
0.7379	Intermediate Similarity	NPD4138	Approved
0.7379	Intermediate Similarity	NPD4688	Approved
0.7379	Intermediate Similarity	NPD5205	Approved
0.7379	Intermediate Similarity	NPD4689	Approved
0.7374	Intermediate Similarity	NPD4195	Approved
0.7368	Intermediate Similarity	NPD5128	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7358	Intermediate Similarity	NPD6050	Approved
0.7355	Intermediate Similarity	NPD8033	Approved
0.7355	Intermediate Similarity	NPD8379	Approved
0.7355	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD8296	Approved
0.7355	Intermediate Similarity	NPD8378	Approved
0.7355	Intermediate Similarity	NPD8380	Approved
0.7355	Intermediate Similarity	NPD8335	Approved
0.7353	Intermediate Similarity	NPD4786	Approved
0.7345	Intermediate Similarity	NPD4768	Approved
0.7345	Intermediate Similarity	NPD4767	Approved
0.7333	Intermediate Similarity	NPD4522	Approved
0.7333	Intermediate Similarity	NPD6051	Approved
0.7328	Intermediate Similarity	NPD5215	Approved
0.7328	Intermediate Similarity	NPD5216	Approved
0.7328	Intermediate Similarity	NPD5217	Approved
0.7327	Intermediate Similarity	NPD3667	Approved
0.7321	Intermediate Similarity	NPD4754	Approved
0.7308	Intermediate Similarity	NPD3573	Approved
0.7282	Intermediate Similarity	NPD1694	Approved
0.7264	Intermediate Similarity	NPD5785	Approved
0.7255	Intermediate Similarity	NPD4788	Approved
0.7248	Intermediate Similarity	NPD4697	Phase 3
0.7241	Intermediate Similarity	NPD6371	Approved
0.7241	Intermediate Similarity	NPD5169	Approved
0.7241	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5135	Approved
0.7227	Intermediate Similarity	NPD6868	Approved
0.7213	Intermediate Similarity	NPD6908	Approved
0.7213	Intermediate Similarity	NPD6909	Approved
0.7212	Intermediate Similarity	NPD5280	Approved
0.7212	Intermediate Similarity	NPD4694	Approved
0.7203	Intermediate Similarity	NPD8133	Approved
0.7182	Intermediate Similarity	NPD7902	Approved
0.7179	Intermediate Similarity	NPD5127	Approved
0.713	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5279	Phase 3
0.7048	Intermediate Similarity	NPD4623	Approved
0.7048	Intermediate Similarity	NPD4519	Discontinued
0.7037	Intermediate Similarity	NPD7637	Suspended
0.7031	Intermediate Similarity	NPD5956	Approved
0.7008	Intermediate Similarity	NPD6033	Approved
0.7	Intermediate Similarity	NPD5654	Approved
0.7	Intermediate Similarity	NPD5167	Approved
0.6983	Remote Similarity	NPD6614	Approved
0.6981	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6067	Discontinued

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