NPASS Compound

Structure

NPC474433 OpenBabel07101718182D 21 22 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 0.5000 0.8660 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 -1.7321 -3.0000 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 -2.5981 -3.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 4 6 1 0 0 0 0 4 11 1 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 12 16 1 6 0 0 0 13 16 1 6 0 0 0 13 17 1 0 0 0 0 14 17 1 6 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 2 1 6 0 0 0 17 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.2
Volume:	315.363
LogP:	1.336
LogD:	0.827
LogS:	-2.66
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	4.06
Fsp3:	0.824
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:	-5.66
MDCK Permeability:	1.043459360516863e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.14
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	65.79521179199219%
Volume Distribution (VD):	0.314
Pgp-substrate:	32.56342315673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	4.817
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.822
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.306
Carcinogencity:	0.097
Eye Corrosion:	0.013
Eye Irritation:	0.264
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC474433

Natural Product ID:	NPC474433
*Common Name:**	3-((1R,4As,5R,6R,8As)-6-Hydroxy-5-(Hydroxymethyl)-5,8A-Dimethyl-2-Methylene-Decahydronaphthalen-1-Yl)Propanoic Acid
IUPAC Name:	3-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]propanoic acid
Synonyms:
Standard InCHIKey:	SGEDHDKBIVWPIX-VUBIOHBQSA-N
Standard InCHI:	InChI=1S/C17H28O4/c1-11-4-6-13-16(2,12(11)5-7-15(20)21)9-8-14(19)17(13,3)10-18/h12-14,18-19H,1,4-10H2,2-3H3,(H,20,21)/t12-,13+,14-,16+,17+/m1/s1
SMILES:	CC12CCC(C(C1CCC(=C)C2CCC(=O)O)(C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468394
PubChem CID:	44577211
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0000495] Carbocyclic fatty acids

*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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	24950.0	nM	PMID[464577]

☑ 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 NPC474433 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	177
0.1-0.2	1441
0.2-0.3	5465
0.3-0.4	15196
0.4-0.5	7582
0.5-0.6	6191
0.6-0.7	4673
0.7-0.8	1796
0.8-0.85	154
0.85-0.9	20
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC91369
0.8765	High Similarity	NPC269360
0.8765	High Similarity	NPC264005
0.8734	High Similarity	NPC243347
0.8718	High Similarity	NPC473420
0.8659	High Similarity	NPC104560
0.8642	High Similarity	NPC73038
0.8642	High Similarity	NPC187545
0.8642	High Similarity	NPC2783
0.8625	High Similarity	NPC130966
0.8611	High Similarity	NPC290445
0.8611	High Similarity	NPC36616
0.8571	High Similarity	NPC247783
0.8571	High Similarity	NPC269543
0.8554	High Similarity	NPC253618
0.8554	High Similarity	NPC121798
0.8554	High Similarity	NPC263393
0.8554	High Similarity	NPC234346
0.8554	High Similarity	NPC475921
0.8554	High Similarity	NPC130520
0.8554	High Similarity	NPC213832
0.8554	High Similarity	NPC474704
0.8554	High Similarity	NPC77001
0.8554	High Similarity	NPC293048
0.8554	High Similarity	NPC127689
0.8554	High Similarity	NPC57954
0.8554	High Similarity	NPC61543
0.8554	High Similarity	NPC270768
0.8554	High Similarity	NPC225585
0.8554	High Similarity	NPC59263
0.8537	High Similarity	NPC33768
0.8519	High Similarity	NPC294438
0.8519	High Similarity	NPC264317
0.8514	High Similarity	NPC72343
0.85	High Similarity	NPC471037
0.85	High Similarity	NPC312480
0.8481	Intermediate Similarity	NPC209318
0.8481	Intermediate Similarity	NPC223330
0.8452	Intermediate Similarity	NPC130278
0.8452	Intermediate Similarity	NPC126369
0.8452	Intermediate Similarity	NPC111110
0.8452	Intermediate Similarity	NPC470589
0.8442	Intermediate Similarity	NPC469867
0.8434	Intermediate Similarity	NPC16377
0.8434	Intermediate Similarity	NPC471900
0.8434	Intermediate Similarity	NPC474719
0.8434	Intermediate Similarity	NPC146937
0.8434	Intermediate Similarity	NPC182797
0.8434	Intermediate Similarity	NPC52169
0.8415	Intermediate Similarity	NPC185638
0.8415	Intermediate Similarity	NPC473226
0.8415	Intermediate Similarity	NPC12774
0.8415	Intermediate Similarity	NPC325594
0.8395	Intermediate Similarity	NPC97505
0.8375	Intermediate Similarity	NPC476292
0.8375	Intermediate Similarity	NPC474605
0.8353	Intermediate Similarity	NPC228784
0.8353	Intermediate Similarity	NPC155120
0.8353	Intermediate Similarity	NPC282616
0.8353	Intermediate Similarity	NPC324341
0.8353	Intermediate Similarity	NPC966
0.8353	Intermediate Similarity	NPC288833
0.8333	Intermediate Similarity	NPC470905
0.8333	Intermediate Similarity	NPC198664
0.8333	Intermediate Similarity	NPC476810
0.8333	Intermediate Similarity	NPC476986
0.8333	Intermediate Similarity	NPC220498
0.8333	Intermediate Similarity	NPC25906
0.8333	Intermediate Similarity	NPC143232
0.8333	Intermediate Similarity	NPC64872
0.8333	Intermediate Similarity	NPC290972
0.8333	Intermediate Similarity	NPC194642
0.8333	Intermediate Similarity	NPC274330
0.8313	Intermediate Similarity	NPC477926
0.8313	Intermediate Similarity	NPC102683
0.8313	Intermediate Similarity	NPC142361
0.8313	Intermediate Similarity	NPC142415
0.8313	Intermediate Similarity	NPC51700
0.8313	Intermediate Similarity	NPC242468
0.8313	Intermediate Similarity	NPC171203
0.8313	Intermediate Similarity	NPC18064
0.8313	Intermediate Similarity	NPC307426
0.8313	Intermediate Similarity	NPC98442
0.8313	Intermediate Similarity	NPC68160
0.8313	Intermediate Similarity	NPC293564
0.8313	Intermediate Similarity	NPC130577
0.8313	Intermediate Similarity	NPC88716
0.8313	Intermediate Similarity	NPC474684
0.8312	Intermediate Similarity	NPC476601
0.8312	Intermediate Similarity	NPC92489
0.8293	Intermediate Similarity	NPC476602
0.8256	Intermediate Similarity	NPC473690
0.8256	Intermediate Similarity	NPC229281
0.8256	Intermediate Similarity	NPC139692
0.8256	Intermediate Similarity	NPC471902
0.8256	Intermediate Similarity	NPC86368
0.8256	Intermediate Similarity	NPC294263
0.8256	Intermediate Similarity	NPC287118
0.825	Intermediate Similarity	NPC328264
0.8235	Intermediate Similarity	NPC210037
0.8235	Intermediate Similarity	NPC291028
0.8235	Intermediate Similarity	NPC477872
0.8235	Intermediate Similarity	NPC7260
0.8235	Intermediate Similarity	NPC227467
0.8235	Intermediate Similarity	NPC169933
0.8235	Intermediate Similarity	NPC273621
0.8235	Intermediate Similarity	NPC290614
0.8235	Intermediate Similarity	NPC86372
0.8235	Intermediate Similarity	NPC18872
0.8235	Intermediate Similarity	NPC172361
0.8235	Intermediate Similarity	NPC120968
0.8228	Intermediate Similarity	NPC263951
0.8214	Intermediate Similarity	NPC40552
0.8214	Intermediate Similarity	NPC473229
0.8214	Intermediate Similarity	NPC181225
0.8214	Intermediate Similarity	NPC246708
0.8214	Intermediate Similarity	NPC473242
0.8214	Intermediate Similarity	NPC474512
0.8214	Intermediate Similarity	NPC242864
0.8214	Intermediate Similarity	NPC470629
0.8214	Intermediate Similarity	NPC4309
0.8214	Intermediate Similarity	NPC17733
0.8214	Intermediate Similarity	NPC290690
0.8205	Intermediate Similarity	NPC472746
0.8193	Intermediate Similarity	NPC28252
0.8193	Intermediate Similarity	NPC322159
0.8193	Intermediate Similarity	NPC72638
0.8193	Intermediate Similarity	NPC55309
0.8193	Intermediate Similarity	NPC80590
0.8193	Intermediate Similarity	NPC82979
0.8182	Intermediate Similarity	NPC39362
0.8171	Intermediate Similarity	NPC171789
0.8161	Intermediate Similarity	NPC272635
0.8161	Intermediate Similarity	NPC277399
0.8161	Intermediate Similarity	NPC169751
0.8161	Intermediate Similarity	NPC231063
0.8161	Intermediate Similarity	NPC159365
0.8161	Intermediate Similarity	NPC145667
0.8161	Intermediate Similarity	NPC20235
0.8161	Intermediate Similarity	NPC282395
0.8161	Intermediate Similarity	NPC6818
0.8161	Intermediate Similarity	NPC114159
0.8161	Intermediate Similarity	NPC299996
0.8161	Intermediate Similarity	NPC80365
0.8161	Intermediate Similarity	NPC222047
0.8161	Intermediate Similarity	NPC191412
0.8161	Intermediate Similarity	NPC32407
0.8161	Intermediate Similarity	NPC263548
0.8161	Intermediate Similarity	NPC88116
0.8148	Intermediate Similarity	NPC48362
0.8148	Intermediate Similarity	NPC475395
0.8148	Intermediate Similarity	NPC170985
0.8148	Intermediate Similarity	NPC73882
0.8148	Intermediate Similarity	NPC476984
0.814	Intermediate Similarity	NPC212301
0.814	Intermediate Similarity	NPC52021
0.814	Intermediate Similarity	NPC475416
0.814	Intermediate Similarity	NPC198242
0.814	Intermediate Similarity	NPC233455
0.814	Intermediate Similarity	NPC211403
0.814	Intermediate Similarity	NPC105189
0.814	Intermediate Similarity	NPC4036
0.814	Intermediate Similarity	NPC6255
0.814	Intermediate Similarity	NPC235884
0.814	Intermediate Similarity	NPC472149
0.814	Intermediate Similarity	NPC475708
0.814	Intermediate Similarity	NPC189520
0.814	Intermediate Similarity	NPC86266
0.814	Intermediate Similarity	NPC65120
0.814	Intermediate Similarity	NPC84319
0.814	Intermediate Similarity	NPC471588
0.814	Intermediate Similarity	NPC145067
0.814	Intermediate Similarity	NPC71074
0.814	Intermediate Similarity	NPC25299
0.814	Intermediate Similarity	NPC158030
0.814	Intermediate Similarity	NPC300351
0.814	Intermediate Similarity	NPC110657
0.814	Intermediate Similarity	NPC187722
0.814	Intermediate Similarity	NPC474525
0.814	Intermediate Similarity	NPC306541
0.814	Intermediate Similarity	NPC471901
0.814	Intermediate Similarity	NPC198054
0.8125	Intermediate Similarity	NPC164999
0.8118	Intermediate Similarity	NPC95246
0.8118	Intermediate Similarity	NPC474972
0.8118	Intermediate Similarity	NPC474686
0.8118	Intermediate Similarity	NPC247312
0.8118	Intermediate Similarity	NPC271974
0.8118	Intermediate Similarity	NPC128496
0.8118	Intermediate Similarity	NPC470588
0.8118	Intermediate Similarity	NPC161751
0.8101	Intermediate Similarity	NPC239098
0.8095	Intermediate Similarity	NPC174619
0.8095	Intermediate Similarity	NPC159046
0.8095	Intermediate Similarity	NPC71507
0.8095	Intermediate Similarity	NPC187376
0.8095	Intermediate Similarity	NPC305029
0.8095	Intermediate Similarity	NPC181103
0.8095	Intermediate Similarity	NPC233836
0.8095	Intermediate Similarity	NPC134197

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 NPC474433 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1996
0.2-0.3	3820
0.3-0.4	2107
0.4-0.5	591
0.5-0.6	224
0.6-0.7	194
0.7-0.8	48
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD7520	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7515	Phase 2
0.7931	Intermediate Similarity	NPD8035	Phase 2
0.7931	Intermediate Similarity	NPD8034	Phase 2
0.7848	Intermediate Similarity	NPD6117	Approved
0.7765	Intermediate Similarity	NPD3618	Phase 1
0.7753	Intermediate Similarity	NPD7748	Approved
0.775	Intermediate Similarity	NPD6116	Phase 1
0.7711	Intermediate Similarity	NPD3667	Approved
0.7654	Intermediate Similarity	NPD6118	Approved
0.7654	Intermediate Similarity	NPD6115	Approved
0.7654	Intermediate Similarity	NPD6114	Approved
0.7654	Intermediate Similarity	NPD6697	Approved
0.7595	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7444	Intermediate Similarity	NPD6399	Phase 3
0.7333	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD6411	Approved
0.7326	Intermediate Similarity	NPD3665	Phase 1
0.7326	Intermediate Similarity	NPD3666	Approved
0.7326	Intermediate Similarity	NPD3133	Approved
0.732	Intermediate Similarity	NPD5739	Approved
0.732	Intermediate Similarity	NPD6675	Approved
0.732	Intermediate Similarity	NPD7128	Approved
0.732	Intermediate Similarity	NPD6402	Approved
0.7312	Intermediate Similarity	NPD4755	Approved
0.7308	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4202	Approved
0.7245	Intermediate Similarity	NPD5697	Approved
0.7245	Intermediate Similarity	NPD5701	Approved
0.7234	Intermediate Similarity	NPD4225	Approved
0.7234	Intermediate Similarity	NPD7638	Approved
0.7209	Intermediate Similarity	NPD4788	Approved
0.7204	Intermediate Similarity	NPD5221	Approved
0.7204	Intermediate Similarity	NPD5222	Approved
0.7204	Intermediate Similarity	NPD4697	Phase 3
0.7204	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7900	Approved
0.7172	Intermediate Similarity	NPD7320	Approved
0.7172	Intermediate Similarity	NPD6881	Approved
0.7172	Intermediate Similarity	NPD6899	Approved
0.7158	Intermediate Similarity	NPD5285	Approved
0.7158	Intermediate Similarity	NPD7639	Approved
0.7158	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD4700	Approved
0.7158	Intermediate Similarity	NPD5286	Approved
0.7158	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.7128	Intermediate Similarity	NPD5173	Approved
0.7128	Intermediate Similarity	NPD6084	Phase 2
0.7128	Intermediate Similarity	NPD6083	Phase 2
0.7126	Intermediate Similarity	NPD3668	Phase 3
0.7125	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4753	Phase 2
0.7111	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD6013	Approved
0.71	Intermediate Similarity	NPD6373	Approved
0.71	Intermediate Similarity	NPD6012	Approved
0.71	Intermediate Similarity	NPD6014	Approved
0.71	Intermediate Similarity	NPD6372	Approved
0.7093	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3703	Phase 2
0.7059	Intermediate Similarity	NPD4695	Discontinued
0.7059	Intermediate Similarity	NPD7525	Registered
0.703	Intermediate Similarity	NPD7102	Approved
0.703	Intermediate Similarity	NPD7290	Approved
0.703	Intermediate Similarity	NPD6883	Approved
0.7013	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5224	Approved
0.701	Intermediate Similarity	NPD5226	Approved
0.701	Intermediate Similarity	NPD5211	Phase 2
0.701	Intermediate Similarity	NPD5225	Approved
0.701	Intermediate Similarity	NPD4633	Approved
0.7	Intermediate Similarity	NPD6011	Approved
0.6966	Remote Similarity	NPD5330	Approved
0.6966	Remote Similarity	NPD7521	Approved
0.6966	Remote Similarity	NPD7146	Approved
0.6966	Remote Similarity	NPD6684	Approved
0.6966	Remote Similarity	NPD5279	Phase 3
0.6966	Remote Similarity	NPD7334	Approved
0.6966	Remote Similarity	NPD6409	Approved
0.6961	Remote Similarity	NPD6869	Approved
0.6961	Remote Similarity	NPD6649	Approved
0.6961	Remote Similarity	NPD6847	Approved
0.6961	Remote Similarity	NPD8130	Phase 1
0.6961	Remote Similarity	NPD6617	Approved
0.6961	Remote Similarity	NPD6650	Approved
0.6939	Remote Similarity	NPD5174	Approved
0.6939	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD4224	Phase 2
0.6915	Remote Similarity	NPD5695	Phase 3
0.6907	Remote Similarity	NPD5223	Approved
0.6893	Remote Similarity	NPD6882	Approved
0.6893	Remote Similarity	NPD8297	Approved
0.6889	Remote Similarity	NPD3573	Approved
0.6882	Remote Similarity	NPD5778	Approved
0.6882	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD5696	Approved
0.6875	Remote Similarity	NPD3698	Phase 2
0.6869	Remote Similarity	NPD5141	Approved
0.6832	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6903	Approved
0.6813	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6672	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6806	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4767	Approved
0.68	Remote Similarity	NPD4768	Approved
0.6796	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4245	Approved
0.679	Remote Similarity	NPD4244	Approved
0.6786	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4754	Approved
0.6765	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5210	Approved
0.6737	Remote Similarity	NPD4629	Approved
0.6707	Remote Similarity	NPD6081	Approved
0.6705	Remote Similarity	NPD4221	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6698	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD3702	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6628	Remote Similarity	NPD3617	Approved
0.6628	Remote Similarity	NPD3671	Phase 1
0.6596	Remote Similarity	NPD7637	Suspended
0.6596	Remote Similarity	NPD5284	Approved
0.6596	Remote Similarity	NPD5281	Approved
0.6585	Remote Similarity	NPD4789	Approved
0.6562	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4197	Approved
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6543	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5360	Phase 3
0.6542	Remote Similarity	NPD6868	Approved
0.6538	Remote Similarity	NPD5248	Approved
0.6538	Remote Similarity	NPD4634	Approved
0.6538	Remote Similarity	NPD5251	Approved
0.6538	Remote Similarity	NPD5247	Approved
0.6538	Remote Similarity	NPD5249	Phase 3
0.6538	Remote Similarity	NPD5250	Approved
0.6538	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6435	Approved
0.6514	Remote Similarity	NPD7101	Approved
0.6514	Remote Similarity	NPD7100	Approved
0.6506	Remote Similarity	NPD5777	Approved
0.6505	Remote Similarity	NPD5168	Approved
0.6484	Remote Similarity	NPD1694	Approved
0.6484	Remote Similarity	NPD5329	Approved
0.6481	Remote Similarity	NPD6317	Approved
0.6481	Remote Similarity	NPD6009	Approved
0.6477	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5217	Approved
0.6476	Remote Similarity	NPD5215	Approved
0.6476	Remote Similarity	NPD5216	Approved
0.6471	Remote Similarity	NPD6008	Approved
0.6463	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6319	Approved
0.6444	Remote Similarity	NPD5362	Discontinued
0.6444	Remote Similarity	NPD7154	Phase 3
0.6422	Remote Similarity	NPD6335	Approved
0.6422	Remote Similarity	NPD6313	Approved
0.6422	Remote Similarity	NPD6314	Approved
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD4688	Approved
0.6413	Remote Similarity	NPD4623	Approved
0.6413	Remote Similarity	NPD6098	Approved
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD4519	Discontinued
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD4689	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.6404	Remote Similarity	NPD5369	Approved
0.6396	Remote Similarity	NPD6909	Approved
0.6396	Remote Similarity	NPD6908	Approved
0.6395	Remote Similarity	NPD6933	Approved
0.6383	Remote Similarity	NPD6080	Approved
0.6383	Remote Similarity	NPD6904	Approved
0.6383	Remote Similarity	NPD6673	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