NPASS Compound

Structure

NPC229584 OpenBabel07101719132D 26 27 0 0 1 0 0 0 0 0999 V2000 -3.4641 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 0.0000 8.0000 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 0.8660 1.5000 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 -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 -1.7321 5.0000 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 6.0000 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 -0.8660 7.5000 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 -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 1 0 0 0 0 0 0 0 0 0 -1.7321 8.0000 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 -0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 2 0 0 0 0 3 17 1 0 0 0 0 6 12 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 15 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 26 1 0 0 0 0 16 18 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 21 1 6 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.25
Volume:	396.57
LogP:	4.001
LogD:	3.569
LogS:	-4.339
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	4.093
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.101
MDCK Permeability:	2.934196891146712e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.386
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.569
Plasma Protein Binding (PPB):	82.54547882080078%
Volume Distribution (VD):	0.361
Pgp-substrate:	23.126930236816406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.51
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.398
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	1.906
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.084
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.901
Carcinogencity:	0.074
Eye Corrosion:	0.096
Eye Irritation:	0.843
Respiratory Toxicity:	0.751

Download Data

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

Natural Product: NPC229584

Natural Product ID:	NPC229584
*Common Name:**	Acetylisocupressic Acid
IUPAC Name:	(1R,4aR,5S,8aR)-5-[(E)-5-acetyloxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	HSANNLXBHKRHSH-SYBQXNLGSA-N
Standard InCHI:	InChI=1S/C22H34O4/c1-15(11-14-26-17(3)23)7-9-18-16(2)8-10-19-21(18,4)12-6-13-22(19,5)20(24)25/h11,18-19H,2,6-10,12-14H2,1,3-5H3,(H,24,25)/b15-11+/t18-,19+,21+,22+/m0/s1
SMILES:	C/C(=CCOC(=O)C)/CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385456
PubChem CID:	73354940
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[534797]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[534797]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[534797]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[534797]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[534797]

☑ 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 NPC229584 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	170
0.1-0.2	1004
0.2-0.3	4107
0.3-0.4	11861
0.4-0.5	11213
0.5-0.6	6827
0.6-0.7	5475
0.7-0.8	1859
0.8-0.85	151
0.85-0.9	21
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC14203
0.9481	High Similarity	NPC40228
0.925	High Similarity	NPC65661
0.9091	High Similarity	NPC239098
0.9036	High Similarity	NPC174342
0.9012	High Similarity	NPC106416
0.9012	High Similarity	NPC86316
0.8974	High Similarity	NPC327674
0.8875	High Similarity	NPC200513
0.878	High Similarity	NPC30984
0.875	High Similarity	NPC327002
0.8721	High Similarity	NPC169343
0.8718	High Similarity	NPC61952
0.8706	High Similarity	NPC51486
0.8706	High Similarity	NPC198818
0.8706	High Similarity	NPC477782
0.869	High Similarity	NPC24816
0.8625	High Similarity	NPC104545
0.8621	High Similarity	NPC476415
0.8608	High Similarity	NPC321514
0.8608	High Similarity	NPC198240
0.8605	High Similarity	NPC477783
0.8588	High Similarity	NPC5509
0.8523	High Similarity	NPC293052
0.8506	High Similarity	NPC139692
0.8488	Intermediate Similarity	NPC232202
0.8488	Intermediate Similarity	NPC476369
0.8488	Intermediate Similarity	NPC476437
0.8462	Intermediate Similarity	NPC476844
0.8452	Intermediate Similarity	NPC322159
0.8421	Intermediate Similarity	NPC91369
0.8415	Intermediate Similarity	NPC123880
0.8415	Intermediate Similarity	NPC471159
0.8409	Intermediate Similarity	NPC91010
0.84	Intermediate Similarity	NPC36616
0.84	Intermediate Similarity	NPC290445
0.8395	Intermediate Similarity	NPC195424
0.8395	Intermediate Similarity	NPC477057
0.8391	Intermediate Similarity	NPC177037
0.8391	Intermediate Similarity	NPC472814
0.8391	Intermediate Similarity	NPC470113
0.8375	Intermediate Similarity	NPC260385
0.8375	Intermediate Similarity	NPC59436
0.8375	Intermediate Similarity	NPC110094
0.8375	Intermediate Similarity	NPC280654
0.8372	Intermediate Similarity	NPC251528
0.8372	Intermediate Similarity	NPC168131
0.8354	Intermediate Similarity	NPC476601
0.8353	Intermediate Similarity	NPC128644
0.8353	Intermediate Similarity	NPC171722
0.8333	Intermediate Similarity	NPC76333
0.8333	Intermediate Similarity	NPC283908
0.8333	Intermediate Similarity	NPC183503
0.8333	Intermediate Similarity	NPC237591
0.8333	Intermediate Similarity	NPC103958
0.8333	Intermediate Similarity	NPC3753
0.8333	Intermediate Similarity	NPC166797
0.8333	Intermediate Similarity	NPC283733
0.8333	Intermediate Similarity	NPC161923
0.8333	Intermediate Similarity	NPC189311
0.8315	Intermediate Similarity	NPC209355
0.8313	Intermediate Similarity	NPC215893
0.8313	Intermediate Similarity	NPC200752
0.8312	Intermediate Similarity	NPC72343
0.8312	Intermediate Similarity	NPC160817
0.8295	Intermediate Similarity	NPC472303
0.8295	Intermediate Similarity	NPC151722
0.8295	Intermediate Similarity	NPC472871
0.8295	Intermediate Similarity	NPC476416
0.8293	Intermediate Similarity	NPC90055
0.8276	Intermediate Similarity	NPC159748
0.8276	Intermediate Similarity	NPC101651
0.8272	Intermediate Similarity	NPC242767
0.8272	Intermediate Similarity	NPC199595
0.8256	Intermediate Similarity	NPC104560
0.8256	Intermediate Similarity	NPC472870
0.825	Intermediate Similarity	NPC471897
0.825	Intermediate Similarity	NPC107039
0.825	Intermediate Similarity	NPC471899
0.8242	Intermediate Similarity	NPC98868
0.8235	Intermediate Similarity	NPC325594
0.8235	Intermediate Similarity	NPC220478
0.8235	Intermediate Similarity	NPC324063
0.8235	Intermediate Similarity	NPC73038
0.8235	Intermediate Similarity	NPC329692
0.8235	Intermediate Similarity	NPC472505
0.8228	Intermediate Similarity	NPC279666
0.8228	Intermediate Similarity	NPC192540
0.8222	Intermediate Similarity	NPC134072
0.8222	Intermediate Similarity	NPC242848
0.8222	Intermediate Similarity	NPC29952
0.8222	Intermediate Similarity	NPC234993
0.8214	Intermediate Similarity	NPC19849
0.8214	Intermediate Similarity	NPC194937
0.8214	Intermediate Similarity	NPC476038
0.8214	Intermediate Similarity	NPC472864
0.8214	Intermediate Similarity	NPC156981
0.8182	Intermediate Similarity	NPC289479
0.8182	Intermediate Similarity	NPC303697
0.8171	Intermediate Similarity	NPC469802
0.8171	Intermediate Similarity	NPC37038
0.8161	Intermediate Similarity	NPC474700
0.8161	Intermediate Similarity	NPC281524
0.8161	Intermediate Similarity	NPC66344
0.8161	Intermediate Similarity	NPC474570
0.8161	Intermediate Similarity	NPC284561
0.8152	Intermediate Similarity	NPC471413
0.8152	Intermediate Similarity	NPC477720
0.8148	Intermediate Similarity	NPC179028
0.8148	Intermediate Similarity	NPC4827
0.814	Intermediate Similarity	NPC167877
0.814	Intermediate Similarity	NPC231599
0.814	Intermediate Similarity	NPC312561
0.8132	Intermediate Similarity	NPC253826
0.8132	Intermediate Similarity	NPC475709
0.8132	Intermediate Similarity	NPC254496
0.8132	Intermediate Similarity	NPC285513
0.8132	Intermediate Similarity	NPC474343
0.8125	Intermediate Similarity	NPC89294
0.8125	Intermediate Similarity	NPC69143
0.8118	Intermediate Similarity	NPC52628
0.8118	Intermediate Similarity	NPC329738
0.8118	Intermediate Similarity	NPC269638
0.8111	Intermediate Similarity	NPC295347
0.8101	Intermediate Similarity	NPC241854
0.8101	Intermediate Similarity	NPC46610
0.8101	Intermediate Similarity	NPC476046
0.8101	Intermediate Similarity	NPC18819
0.8101	Intermediate Similarity	NPC251970
0.8095	Intermediate Similarity	NPC23748
0.8095	Intermediate Similarity	NPC97913
0.8095	Intermediate Similarity	NPC311070
0.8095	Intermediate Similarity	NPC222358
0.8095	Intermediate Similarity	NPC476927
0.8095	Intermediate Similarity	NPC49208
0.8095	Intermediate Similarity	NPC22611
0.809	Intermediate Similarity	NPC115021
0.8072	Intermediate Similarity	NPC221647
0.8072	Intermediate Similarity	NPC170303
0.8072	Intermediate Similarity	NPC278459
0.8068	Intermediate Similarity	NPC281942
0.8068	Intermediate Similarity	NPC120840
0.8068	Intermediate Similarity	NPC472866
0.8068	Intermediate Similarity	NPC113989
0.8068	Intermediate Similarity	NPC474728
0.8068	Intermediate Similarity	NPC232426
0.8068	Intermediate Similarity	NPC471896
0.8065	Intermediate Similarity	NPC303559
0.8065	Intermediate Similarity	NPC471412
0.8065	Intermediate Similarity	NPC93744
0.8065	Intermediate Similarity	NPC63249
0.8065	Intermediate Similarity	NPC476888
0.8049	Intermediate Similarity	NPC476438
0.8049	Intermediate Similarity	NPC263951
0.8049	Intermediate Similarity	NPC158846
0.8049	Intermediate Similarity	NPC16394
0.8049	Intermediate Similarity	NPC192999
0.8049	Intermediate Similarity	NPC231431
0.8046	Intermediate Similarity	NPC472302
0.8046	Intermediate Similarity	NPC477128
0.8046	Intermediate Similarity	NPC226863
0.8043	Intermediate Similarity	NPC316598
0.8043	Intermediate Similarity	NPC57079
0.8043	Intermediate Similarity	NPC108368
0.8025	Intermediate Similarity	NPC316500
0.8025	Intermediate Similarity	NPC165711
0.8023	Intermediate Similarity	NPC186975
0.8023	Intermediate Similarity	NPC185638
0.8023	Intermediate Similarity	NPC476104
0.8023	Intermediate Similarity	NPC202394
0.8023	Intermediate Similarity	NPC82979
0.8023	Intermediate Similarity	NPC473226
0.8023	Intermediate Similarity	NPC472869
0.8023	Intermediate Similarity	NPC131813
0.8	Intermediate Similarity	NPC248758
0.8	Intermediate Similarity	NPC165064
0.8	Intermediate Similarity	NPC228978
0.8	Intermediate Similarity	NPC164577
0.8	Intermediate Similarity	NPC476795
0.8	Intermediate Similarity	NPC102048
0.8	Intermediate Similarity	NPC472865
0.8	Intermediate Similarity	NPC149869
0.7979	Intermediate Similarity	NPC155332
0.7979	Intermediate Similarity	NPC32577
0.7979	Intermediate Similarity	NPC114540
0.7979	Intermediate Similarity	NPC476769
0.7979	Intermediate Similarity	NPC476081
0.7979	Intermediate Similarity	NPC134077
0.7979	Intermediate Similarity	NPC40918
0.7979	Intermediate Similarity	NPC476890
0.7979	Intermediate Similarity	NPC162973
0.7978	Intermediate Similarity	NPC285184
0.7978	Intermediate Similarity	NPC165904
0.7978	Intermediate Similarity	NPC141831
0.7978	Intermediate Similarity	NPC476187
0.7978	Intermediate Similarity	NPC470590
0.7978	Intermediate Similarity	NPC77099
0.7978	Intermediate Similarity	NPC473986
0.7978	Intermediate Similarity	NPC60755
0.7978	Intermediate Similarity	NPC179517

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 NPC229584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1308
0.2-0.3	3568
0.3-0.4	2640
0.4-0.5	928
0.5-0.6	316
0.6-0.7	202
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8875	High Similarity	NPD4752	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8039	Approved
0.7889	Intermediate Similarity	NPD6399	Phase 3
0.7849	Intermediate Similarity	NPD7638	Approved
0.7802	Intermediate Similarity	NPD7748	Approved
0.7766	Intermediate Similarity	NPD7640	Approved
0.7766	Intermediate Similarity	NPD7639	Approved
0.764	Intermediate Similarity	NPD5737	Approved
0.764	Intermediate Similarity	NPD6672	Approved
0.7614	Intermediate Similarity	NPD7146	Approved
0.7614	Intermediate Similarity	NPD7334	Approved
0.7614	Intermediate Similarity	NPD7521	Approved
0.7614	Intermediate Similarity	NPD6684	Approved
0.7614	Intermediate Similarity	NPD6409	Approved
0.7614	Intermediate Similarity	NPD5330	Approved
0.7582	Intermediate Similarity	NPD7515	Phase 2
0.7576	Intermediate Similarity	NPD6686	Approved
0.7553	Intermediate Similarity	NPD6084	Phase 2
0.7553	Intermediate Similarity	NPD6083	Phase 2
0.7553	Intermediate Similarity	NPD7902	Approved
0.7474	Intermediate Similarity	NPD4225	Approved
0.7444	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6903	Approved
0.7391	Intermediate Similarity	NPD5693	Phase 1
0.7391	Intermediate Similarity	NPD6411	Approved
0.7386	Intermediate Similarity	NPD4786	Approved
0.7363	Intermediate Similarity	NPD6051	Approved
0.7356	Intermediate Similarity	NPD3667	Approved
0.734	Intermediate Similarity	NPD5695	Phase 3
0.7326	Intermediate Similarity	NPD4695	Discontinued
0.7312	Intermediate Similarity	NPD5779	Approved
0.7312	Intermediate Similarity	NPD5778	Approved
0.7303	Intermediate Similarity	NPD1694	Approved
0.7294	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5696	Approved
0.7234	Intermediate Similarity	NPD7900	Approved
0.7234	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6098	Approved
0.7204	Intermediate Similarity	NPD7637	Suspended
0.7204	Intermediate Similarity	NPD8035	Phase 2
0.7204	Intermediate Similarity	NPD8034	Phase 2
0.7191	Intermediate Similarity	NPD3133	Approved
0.7191	Intermediate Similarity	NPD3666	Approved
0.7191	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6101	Approved
0.7174	Intermediate Similarity	NPD6904	Approved
0.7174	Intermediate Similarity	NPD6673	Approved
0.7174	Intermediate Similarity	NPD6080	Approved
0.7111	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD46	Approved
0.7097	Intermediate Similarity	NPD6698	Approved
0.7097	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD7154	Phase 3
0.7079	Intermediate Similarity	NPD5362	Discontinued
0.7071	Intermediate Similarity	NPD7632	Discontinued
0.7033	Intermediate Similarity	NPD3618	Phase 1
0.7033	Intermediate Similarity	NPD4623	Approved
0.7033	Intermediate Similarity	NPD4519	Discontinued
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD3668	Phase 3
0.6989	Remote Similarity	NPD4753	Phase 2
0.6989	Remote Similarity	NPD5328	Approved
0.6979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4223	Phase 3
0.6966	Remote Similarity	NPD4221	Approved
0.6962	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3573	Approved
0.6923	Remote Similarity	NPD5329	Approved
0.6923	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6882	Remote Similarity	NPD5208	Approved
0.6848	Remote Similarity	NPD5279	Phase 3
0.6842	Remote Similarity	NPD5284	Approved
0.6842	Remote Similarity	NPD6050	Approved
0.6842	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD5281	Approved
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6372	Approved
0.6813	Remote Similarity	NPD4197	Approved
0.6813	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5701	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.6778	Remote Similarity	NPD4270	Approved
0.6778	Remote Similarity	NPD4269	Approved
0.6778	Remote Similarity	NPD6435	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6742	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5692	Phase 3
0.6735	Remote Similarity	NPD7614	Phase 1
0.6731	Remote Similarity	NPD6011	Approved
0.6705	Remote Similarity	NPD3617	Approved
0.6703	Remote Similarity	NPD4788	Approved
0.6703	Remote Similarity	NPD6695	Phase 3
0.67	Remote Similarity	NPD6404	Discontinued
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD6422	Discontinued
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6053	Discontinued
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD6412	Phase 2
0.6633	Remote Similarity	NPD4629	Approved
0.6633	Remote Similarity	NPD5210	Approved
0.663	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7645	Phase 2
0.6628	Remote Similarity	NPD6924	Approved
0.6628	Remote Similarity	NPD6926	Approved
0.6598	Remote Similarity	NPD4202	Approved
0.6593	Remote Similarity	NPD5209	Approved
0.6571	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4697	Phase 3
0.6566	Remote Similarity	NPD5221	Approved
0.6566	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD7732	Phase 3
0.6562	Remote Similarity	NPD5207	Approved
0.6559	Remote Similarity	NPD5363	Approved
0.6556	Remote Similarity	NPD4821	Approved
0.6556	Remote Similarity	NPD4252	Approved
0.6556	Remote Similarity	NPD4819	Approved
0.6556	Remote Similarity	NPD4822	Approved
0.6556	Remote Similarity	NPD7525	Registered
0.6556	Remote Similarity	NPD4820	Approved
0.6556	Remote Similarity	NPD5368	Approved
0.6552	Remote Similarity	NPD6942	Approved
0.6552	Remote Similarity	NPD7339	Approved
0.6552	Remote Similarity	NPD3702	Approved
0.6531	Remote Similarity	NPD6001	Approved
0.6522	Remote Similarity	NPD5332	Approved
0.6522	Remote Similarity	NPD7507	Approved
0.6522	Remote Similarity	NPD5331	Approved
0.6517	Remote Similarity	NPD4268	Approved
0.6517	Remote Similarity	NPD4271	Approved
0.65	Remote Similarity	NPD4755	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6495	Remote Similarity	NPD7983	Approved
0.6489	Remote Similarity	NPD5280	Approved
0.6489	Remote Similarity	NPD5690	Phase 2
0.6489	Remote Similarity	NPD4694	Approved
0.6484	Remote Similarity	NPD4790	Discontinued
0.6477	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6117	Approved
0.6477	Remote Similarity	NPD6933	Approved
0.6476	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6868	Approved
0.6449	Remote Similarity	NPD6371	Approved
0.6447	Remote Similarity	NPD4266	Approved
0.6447	Remote Similarity	NPD3194	Approved
0.6447	Remote Similarity	NPD3195	Phase 2
0.6447	Remote Similarity	NPD3196	Approved
0.6444	Remote Similarity	NPD6929	Approved
0.6437	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8133	Approved
0.6421	Remote Similarity	NPD7750	Discontinued
0.6421	Remote Similarity	NPD7524	Approved
0.6408	Remote Similarity	NPD5211	Phase 2
0.6404	Remote Similarity	NPD6116	Phase 1
0.64	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7839	Suspended
0.6395	Remote Similarity	NPD6081	Approved
0.6395	Remote Similarity	NPD5777	Approved
0.6395	Remote Similarity	NPD4243	Approved
0.6392	Remote Similarity	NPD7838	Discovery
0.6386	Remote Similarity	NPD7331	Phase 2
0.6386	Remote Similarity	NPD4224	Phase 2
0.6381	Remote Similarity	NPD6008	Approved
0.6374	Remote Similarity	NPD6930	Phase 2
0.6374	Remote Similarity	NPD6931	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