NPASS Compound

Structure

NPC247783 OpenBabel07101718322D 23 24 0 0 1 0 0 0 0 0999 V2000 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 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 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 1 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 2 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 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 O 0 0 0 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 6 2 0 0 0 0 2 13 2 0 0 0 0 3 14 2 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 1 0 0 0 16 21 1 6 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.18
LogD:	2.838
LogS:	-3.503
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	4.609
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.401
MDCK Permeability:	2.319246414117515e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.158
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	65.35641479492188%
Volume Distribution (VD):	0.665
Pgp-substrate:	35.94792556762695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.142
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.528
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.534
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	1.733
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.785
Carcinogencity:	0.828
Eye Corrosion:	0.325
Eye Irritation:	0.54
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC247783

Natural Product ID:	NPC247783
*Common Name:**	12Rhydroxylabda-8(17),13(16),14-Trien-19-Oic Acid
IUPAC Name:	(1S,4aR,5S,8aR)-5-[(2R)-2-hydroxy-3-methylidenepent-4-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	BJIYGXNZLPKDHO-PNDFQMOFSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-6-13(2)16(21)12-15-14(3)8-9-17-19(15,4)10-7-11-20(17,5)18(22)23/h6,15-17,21H,1-3,7-12H2,4-5H3,(H,22,23)/t15-,16+,17+,19+,20-/m0/s1
SMILES:	C=CC(=C)[C@@H](C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385631
PubChem CID:	71725776
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
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[511956]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[511956]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[511956]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[511956]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[511956]

☑ 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 NPC247783 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	162
0.1-0.2	1034
0.2-0.3	4663
0.3-0.4	14389
0.4-0.5	9416
0.5-0.6	7056
0.6-0.7	4556
0.7-0.8	1341
0.8-0.85	67
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC269543
0.8919	High Similarity	NPC46610
0.8919	High Similarity	NPC18819
0.8767	High Similarity	NPC91369
0.8765	High Similarity	NPC82979
0.8734	High Similarity	NPC123880
0.8734	High Similarity	NPC471159
0.8701	High Similarity	NPC239098
0.8625	High Similarity	NPC312480
0.8571	High Similarity	NPC474433
0.85	High Similarity	NPC170985
0.8421	Intermediate Similarity	NPC237591
0.8421	Intermediate Similarity	NPC3753
0.84	Intermediate Similarity	NPC72343
0.8375	Intermediate Similarity	NPC473420
0.8313	Intermediate Similarity	NPC473226
0.8312	Intermediate Similarity	NPC476844
0.8293	Intermediate Similarity	NPC165064
0.8293	Intermediate Similarity	NPC263974
0.8272	Intermediate Similarity	NPC73882
0.8267	Intermediate Similarity	NPC235586
0.8243	Intermediate Similarity	NPC36616
0.8243	Intermediate Similarity	NPC290445
0.8228	Intermediate Similarity	NPC179028
0.8205	Intermediate Similarity	NPC476601
0.8205	Intermediate Similarity	NPC69143
0.8182	Intermediate Similarity	NPC103958
0.8182	Intermediate Similarity	NPC161923
0.8182	Intermediate Similarity	NPC283908
0.8182	Intermediate Similarity	NPC183503
0.8171	Intermediate Similarity	NPC243347
0.8171	Intermediate Similarity	NPC245866
0.8171	Intermediate Similarity	NPC215893
0.8148	Intermediate Similarity	NPC223330
0.8148	Intermediate Similarity	NPC14151
0.8148	Intermediate Similarity	NPC209318
0.8125	Intermediate Similarity	NPC192999
0.8125	Intermediate Similarity	NPC476438
0.8118	Intermediate Similarity	NPC104560
0.8101	Intermediate Similarity	NPC61952
0.8101	Intermediate Similarity	NPC74995
0.8095	Intermediate Similarity	NPC322159
0.8095	Intermediate Similarity	NPC475007
0.8095	Intermediate Similarity	NPC185638
0.8095	Intermediate Similarity	NPC187545
0.8095	Intermediate Similarity	NPC155011
0.8095	Intermediate Similarity	NPC70661
0.8077	Intermediate Similarity	NPC279666
0.8077	Intermediate Similarity	NPC39362
0.8077	Intermediate Similarity	NPC192540
0.8072	Intermediate Similarity	NPC476038
0.8072	Intermediate Similarity	NPC130966
0.8072	Intermediate Similarity	NPC194937
0.8052	Intermediate Similarity	NPC472813
0.8052	Intermediate Similarity	NPC177826
0.8046	Intermediate Similarity	NPC301244
0.8023	Intermediate Similarity	NPC128496
0.8023	Intermediate Similarity	NPC281524
0.8	Intermediate Similarity	NPC59436
0.8	Intermediate Similarity	NPC71507
0.8	Intermediate Similarity	NPC128644
0.8	Intermediate Similarity	NPC477926
0.8	Intermediate Similarity	NPC181103
0.8	Intermediate Similarity	NPC198240
0.8	Intermediate Similarity	NPC476810
0.7976	Intermediate Similarity	NPC269638
0.7976	Intermediate Similarity	NPC283733
0.7976	Intermediate Similarity	NPC52628
0.7975	Intermediate Similarity	NPC263582
0.7973	Intermediate Similarity	NPC476406
0.7952	Intermediate Similarity	NPC470948
0.7949	Intermediate Similarity	NPC255168
0.7949	Intermediate Similarity	NPC251970
0.7949	Intermediate Similarity	NPC476046
0.7949	Intermediate Similarity	NPC241854
0.7931	Intermediate Similarity	NPC232202
0.7927	Intermediate Similarity	NPC90055
0.7927	Intermediate Similarity	NPC14203
0.7927	Intermediate Similarity	NPC229584
0.7927	Intermediate Similarity	NPC159148
0.7927	Intermediate Similarity	NPC121984
0.7907	Intermediate Similarity	NPC16377
0.7907	Intermediate Similarity	NPC181225
0.7907	Intermediate Similarity	NPC17733
0.7907	Intermediate Similarity	NPC474512
0.7907	Intermediate Similarity	NPC473242
0.7907	Intermediate Similarity	NPC290690
0.7907	Intermediate Similarity	NPC470629
0.7901	Intermediate Similarity	NPC263951
0.7901	Intermediate Similarity	NPC474113
0.7901	Intermediate Similarity	NPC308038
0.7901	Intermediate Similarity	NPC152061
0.7901	Intermediate Similarity	NPC100906
0.7895	Intermediate Similarity	NPC9942
0.7889	Intermediate Similarity	NPC301534
0.7889	Intermediate Similarity	NPC250757
0.7882	Intermediate Similarity	NPC329692
0.7882	Intermediate Similarity	NPC73038
0.7882	Intermediate Similarity	NPC85698
0.7882	Intermediate Similarity	NPC470955
0.7882	Intermediate Similarity	NPC202394
0.7882	Intermediate Similarity	NPC325594
0.7875	Intermediate Similarity	NPC165711
0.7875	Intermediate Similarity	NPC97377
0.7875	Intermediate Similarity	NPC469867
0.7875	Intermediate Similarity	NPC472746
0.7865	Intermediate Similarity	NPC87095
0.7865	Intermediate Similarity	NPC470958
0.7865	Intermediate Similarity	NPC80365
0.7865	Intermediate Similarity	NPC470957
0.7857	Intermediate Similarity	NPC139566
0.7857	Intermediate Similarity	NPC97505
0.7848	Intermediate Similarity	NPC476795
0.7841	Intermediate Similarity	NPC472814
0.7841	Intermediate Similarity	NPC177037
0.7831	Intermediate Similarity	NPC212083
0.7831	Intermediate Similarity	NPC46881
0.7831	Intermediate Similarity	NPC145143
0.7831	Intermediate Similarity	NPC474605
0.7831	Intermediate Similarity	NPC476984
0.7831	Intermediate Similarity	NPC475395
0.7831	Intermediate Similarity	NPC476292
0.7831	Intermediate Similarity	NPC151519
0.7831	Intermediate Similarity	NPC477858
0.7826	Intermediate Similarity	NPC266955
0.7821	Intermediate Similarity	NPC244708
0.7821	Intermediate Similarity	NPC330659
0.7821	Intermediate Similarity	NPC161187
0.7821	Intermediate Similarity	NPC36310
0.7816	Intermediate Similarity	NPC194642
0.7816	Intermediate Similarity	NPC95246
0.7816	Intermediate Similarity	NPC36668
0.7816	Intermediate Similarity	NPC274330
0.7816	Intermediate Similarity	NPC474972
0.7816	Intermediate Similarity	NPC118011
0.7816	Intermediate Similarity	NPC143232
0.7816	Intermediate Similarity	NPC470588
0.7816	Intermediate Similarity	NPC474686
0.7816	Intermediate Similarity	NPC198664
0.7816	Intermediate Similarity	NPC161751
0.7805	Intermediate Similarity	NPC148685
0.7805	Intermediate Similarity	NPC2482
0.7805	Intermediate Similarity	NPC104120
0.7805	Intermediate Similarity	NPC157895
0.7805	Intermediate Similarity	NPC281880
0.7805	Intermediate Similarity	NPC271104
0.7791	Intermediate Similarity	NPC305029
0.7791	Intermediate Similarity	NPC18064
0.7791	Intermediate Similarity	NPC293564
0.7791	Intermediate Similarity	NPC98442
0.7791	Intermediate Similarity	NPC88716
0.7791	Intermediate Similarity	NPC142415
0.7791	Intermediate Similarity	NPC171203
0.7791	Intermediate Similarity	NPC68160
0.7791	Intermediate Similarity	NPC312561
0.7791	Intermediate Similarity	NPC142361
0.7791	Intermediate Similarity	NPC242468
0.7791	Intermediate Similarity	NPC51700
0.7791	Intermediate Similarity	NPC474684
0.7791	Intermediate Similarity	NPC307426
0.7791	Intermediate Similarity	NPC102683
0.7791	Intermediate Similarity	NPC130577
0.7778	Intermediate Similarity	NPC476986
0.7778	Intermediate Similarity	NPC297996
0.7778	Intermediate Similarity	NPC209355
0.7778	Intermediate Similarity	NPC53565
0.7778	Intermediate Similarity	NPC475994
0.7778	Intermediate Similarity	NPC62336
0.7778	Intermediate Similarity	NPC321514
0.7778	Intermediate Similarity	NPC470905
0.7765	Intermediate Similarity	NPC106416
0.7765	Intermediate Similarity	NPC476426
0.7765	Intermediate Similarity	NPC471344
0.7765	Intermediate Similarity	NPC264317
0.7765	Intermediate Similarity	NPC86316
0.7765	Intermediate Similarity	NPC294438
0.7765	Intermediate Similarity	NPC471224
0.7765	Intermediate Similarity	NPC274724
0.7765	Intermediate Similarity	NPC476602
0.7765	Intermediate Similarity	NPC329738
0.775	Intermediate Similarity	NPC104806
0.775	Intermediate Similarity	NPC20466
0.775	Intermediate Similarity	NPC309399
0.7742	Intermediate Similarity	NPC115899
0.7738	Intermediate Similarity	NPC105173
0.7738	Intermediate Similarity	NPC472498
0.7738	Intermediate Similarity	NPC79945
0.7738	Intermediate Similarity	NPC471037
0.7733	Intermediate Similarity	NPC103734
0.7727	Intermediate Similarity	NPC111110
0.7727	Intermediate Similarity	NPC470589
0.7727	Intermediate Similarity	NPC182136
0.7727	Intermediate Similarity	NPC153853
0.7727	Intermediate Similarity	NPC126369
0.7722	Intermediate Similarity	NPC166797
0.7722	Intermediate Similarity	NPC301065
0.7717	Intermediate Similarity	NPC316598
0.7711	Intermediate Similarity	NPC40228
0.7711	Intermediate Similarity	NPC142244
0.7711	Intermediate Similarity	NPC474484

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 NPC247783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1474
0.2-0.3	3720
0.3-0.4	2487
0.4-0.5	784
0.5-0.6	290
0.6-0.7	214
0.7-0.8	30
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
0.7831	Intermediate Similarity	NPD3667	Approved
0.7765	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4786	Approved
0.7444	Intermediate Similarity	NPD7515	Phase 2
0.7444	Intermediate Similarity	NPD6411	Approved
0.7442	Intermediate Similarity	NPD3666	Approved
0.7442	Intermediate Similarity	NPD3133	Approved
0.7442	Intermediate Similarity	NPD3665	Phase 1
0.7363	Intermediate Similarity	NPD5779	Approved
0.7363	Intermediate Similarity	NPD5778	Approved
0.7363	Intermediate Similarity	NPD6399	Phase 3
0.7349	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD5279	Phase 3
0.7253	Intermediate Similarity	NPD7637	Suspended
0.7222	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6101	Approved
0.7209	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4695	Discontinued
0.7126	Intermediate Similarity	NPD4788	Approved
0.7126	Intermediate Similarity	NPD5362	Discontinued
0.7097	Intermediate Similarity	NPD7748	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD4623	Approved
0.7079	Intermediate Similarity	NPD4519	Discontinued
0.7079	Intermediate Similarity	NPD7334	Approved
0.7073	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6926	Approved
0.7073	Intermediate Similarity	NPD6924	Approved
0.7065	Intermediate Similarity	NPD6079	Approved
0.7065	Intermediate Similarity	NPD8034	Phase 2
0.7065	Intermediate Similarity	NPD8035	Phase 2
0.7059	Intermediate Similarity	NPD6929	Approved
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7033	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5328	Approved
0.7011	Intermediate Similarity	NPD4269	Approved
0.7011	Intermediate Similarity	NPD4270	Approved
0.6988	Remote Similarity	NPD8264	Approved
0.6979	Remote Similarity	NPD4225	Approved
0.6977	Remote Similarity	NPD6930	Phase 2
0.6977	Remote Similarity	NPD6931	Approved
0.6941	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7145	Approved
0.6932	Remote Similarity	NPD7154	Phase 3
0.6923	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6903	Approved
0.6914	Remote Similarity	NPD7143	Approved
0.6914	Remote Similarity	NPD7144	Approved
0.6907	Remote Similarity	NPD7640	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.6905	Remote Similarity	NPD6117	Approved
0.6905	Remote Similarity	NPD6933	Approved
0.6905	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5284	Approved
0.6882	Remote Similarity	NPD5281	Approved
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD6083	Phase 2
0.6848	Remote Similarity	NPD4753	Phase 2
0.6835	Remote Similarity	NPD4224	Phase 2
0.6829	Remote Similarity	NPD7152	Approved
0.6829	Remote Similarity	NPD7151	Approved
0.6829	Remote Similarity	NPD7150	Approved
0.6824	Remote Similarity	NPD6116	Phase 1
0.6824	Remote Similarity	NPD5776	Phase 2
0.6824	Remote Similarity	NPD6925	Approved
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD4221	Approved
0.6809	Remote Similarity	NPD4202	Approved
0.6804	Remote Similarity	NPD7638	Approved
0.679	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3698	Phase 2
0.679	Remote Similarity	NPD6923	Approved
0.679	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6922	Approved
0.6786	Remote Similarity	NPD7339	Approved
0.6786	Remote Similarity	NPD6942	Approved
0.6786	Remote Similarity	NPD8039	Approved
0.6782	Remote Similarity	NPD7332	Phase 2
0.6782	Remote Similarity	NPD4819	Approved
0.6782	Remote Similarity	NPD7514	Phase 3
0.6782	Remote Similarity	NPD4252	Approved
0.6782	Remote Similarity	NPD4820	Approved
0.6782	Remote Similarity	NPD4822	Approved
0.6782	Remote Similarity	NPD4821	Approved
0.6778	Remote Similarity	NPD5363	Approved
0.6774	Remote Similarity	NPD5785	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6768	Remote Similarity	NPD5211	Phase 2
0.6744	Remote Similarity	NPD6697	Approved
0.6744	Remote Similarity	NPD6118	Approved
0.6744	Remote Similarity	NPD6114	Approved
0.6744	Remote Similarity	NPD4271	Approved
0.6744	Remote Similarity	NPD6115	Approved
0.6744	Remote Similarity	NPD4268	Approved
0.6742	Remote Similarity	NPD5332	Approved
0.6742	Remote Similarity	NPD6695	Phase 3
0.6742	Remote Similarity	NPD5331	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD6672	Approved
0.6707	Remote Similarity	NPD4244	Approved
0.6707	Remote Similarity	NPD4245	Approved
0.6705	Remote Similarity	NPD4790	Discontinued
0.6705	Remote Similarity	NPD5369	Approved
0.6705	Remote Similarity	NPD6902	Approved
0.6703	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.6633	Remote Similarity	NPD5696	Approved
0.663	Remote Similarity	NPD3573	Approved
0.6628	Remote Similarity	NPD6932	Approved
0.6627	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6881	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD6686	Approved
0.6598	Remote Similarity	NPD4697	Phase 3
0.6593	Remote Similarity	NPD5329	Approved
0.6593	Remote Similarity	NPD6893	Approved
0.6593	Remote Similarity	NPD1694	Approved
0.6591	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5368	Approved
0.6591	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7509	Discontinued
0.6588	Remote Similarity	NPD3702	Approved
0.6574	Remote Similarity	NPD7115	Discovery
0.6569	Remote Similarity	NPD6675	Approved
0.6569	Remote Similarity	NPD5739	Approved
0.6569	Remote Similarity	NPD6402	Approved
0.6569	Remote Similarity	NPD7128	Approved
0.6566	Remote Similarity	NPD5285	Approved
0.6566	Remote Similarity	NPD5286	Approved
0.6566	Remote Similarity	NPD4696	Approved
0.6562	Remote Similarity	NPD7900	Approved
0.6562	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3617	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6531	Remote Similarity	NPD4755	Approved
0.6526	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD4138	Approved
0.6522	Remote Similarity	NPD6098	Approved
0.6522	Remote Similarity	NPD4689	Approved
0.6522	Remote Similarity	NPD4690	Approved
0.6522	Remote Similarity	NPD5280	Approved
0.6522	Remote Similarity	NPD4693	Phase 3
0.6522	Remote Similarity	NPD4688	Approved
0.6522	Remote Similarity	NPD5205	Approved
0.6522	Remote Similarity	NPD5690	Phase 2
0.6522	Remote Similarity	NPD4694	Approved
0.6517	Remote Similarity	NPD6898	Phase 1
0.6506	Remote Similarity	NPD4789	Approved
0.6505	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD5223	Approved
0.6495	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2629	Approved
0.6477	Remote Similarity	NPD7645	Phase 2
0.6476	Remote Similarity	NPD7290	Approved
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD6883	Approved
0.6452	Remote Similarity	NPD7750	Discontinued
0.6452	Remote Similarity	NPD7524	Approved
0.6452	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6435	Approved
0.6442	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7320	Approved
0.6436	Remote Similarity	NPD5225	Approved
0.6436	Remote Similarity	NPD5226	Approved
0.6436	Remote Similarity	NPD4633	Approved
0.6436	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD7839	Suspended
0.6429	Remote Similarity	NPD5777	Approved
0.6429	Remote Similarity	NPD6081	Approved
0.6421	Remote Similarity	NPD5207	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6650	Approved
0.641	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7525	Registered
0.64	Remote Similarity	NPD4700	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