NPASS Compound

Structure

NPC118159 OpenBabel07101718292D 27 28 0 0 1 0 0 0 0 0999 V2000 -4.0388 -3.0981 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 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 -4.0388 -1.3660 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 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -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 -0.9511 0.3090 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 -3.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 11 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 14 23 2 0 0 0 0 15 24 2 0 0 0 0 15 26 1 0 0 0 0 16 10 1 6 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 6 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 11 1 6 0 0 0 19 21 1 0 0 0 0 20 14 1 6 0 0 0 20 21 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	402.724
LogP:	3.135
LogD:	2.883
LogS:	-3.186
# Rotatable Bonds:	7
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	4.726
Fsp3:	0.682
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:	-4.579
MDCK Permeability:	2.287738971062936e-05
Pgp-inhibitor:	0.667
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.601

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.395
Plasma Protein Binding (PPB):	82.99198913574219%
Volume Distribution (VD):	1.146
Pgp-substrate:	15.148931503295898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.223
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.596
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.51

ADMET: Excretion

Clearance (CL):	9.043
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.864
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.167
Carcinogencity:	0.104
Eye Corrosion:	0.484
Eye Irritation:	0.142
Respiratory Toxicity:	0.449

Download Data

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

Natural Product: NPC118159

Natural Product ID:	NPC118159
*Common Name:**	3-Angeloyloxy-8-Acetoxy-10(14)-Oplopen-4-One
IUPAC Name:	[(2S,3R,3aR,4S,5R,7aR)-3-acetyl-5-acetyloxy-7-methylidene-4-propan-2-yl-1,2,3,3a,4,5,6,7a-octahydroinden-2-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	FDFXUUAZUMJPNJ-OZWCXVTBSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-8-12(4)22(25)27-18-10-16-13(5)9-17(26-15(7)24)19(11(2)3)21(16)20(18)14(6)23/h8,11,16-21H,5,9-10H2,1-4,6-7H3/b12-8-/t16-,17+,18-,19+,20-,21+/m0/s1
SMILES:	C/C=C(/C)C(=O)O[C@H]1C[C@H]2C(=C)C[C@H]([C@@H](C(C)C)[C@@H]2[C@H]1C(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514283
PubChem CID:	643686
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO16686	Robinsonecio gerberifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608854]
NPO16686	Robinsonecio gerberifolius	Species	Asteraceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	13000.0	nM	PMID[490520]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	13000.0	nM	PMID[490520]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	33900.0	nM	PMID[490520]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	43600.0	nM	PMID[490520]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	78700.0	nM	PMID[490520]

☑ 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 NPC118159 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	216
0.1-0.2	1492
0.2-0.3	5014
0.3-0.4	8572
0.4-0.5	13339
0.5-0.6	7721
0.6-0.7	5240
0.7-0.8	1078
0.8-0.85	13
0.85-0.9	7
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9468	High Similarity	NPC475750
0.9149	High Similarity	NPC471932
0.8632	High Similarity	NPC470978
0.8632	High Similarity	NPC470974
0.86	High Similarity	NPC470975
0.86	High Similarity	NPC103088
0.86	High Similarity	NPC470979
0.8511	High Similarity	NPC221282
0.8462	Intermediate Similarity	NPC471933
0.8384	Intermediate Similarity	NPC475099
0.835	Intermediate Similarity	NPC471934
0.8298	Intermediate Similarity	NPC288699
0.8269	Intermediate Similarity	NPC179642
0.8241	Intermediate Similarity	NPC470420
0.8125	Intermediate Similarity	NPC470230
0.8	Intermediate Similarity	NPC176845
0.7961	Intermediate Similarity	NPC470297
0.7938	Intermediate Similarity	NPC290651
0.7938	Intermediate Similarity	NPC472953
0.7938	Intermediate Similarity	NPC473944
0.7921	Intermediate Similarity	NPC471413
0.7921	Intermediate Similarity	NPC306856
0.7917	Intermediate Similarity	NPC471043
0.79	Intermediate Similarity	NPC2049
0.789	Intermediate Similarity	NPC469794
0.789	Intermediate Similarity	NPC190286
0.789	Intermediate Similarity	NPC72772
0.7879	Intermediate Similarity	NPC470229
0.7876	Intermediate Similarity	NPC204812
0.787	Intermediate Similarity	NPC472926
0.787	Intermediate Similarity	NPC470120
0.7864	Intermediate Similarity	NPC254202
0.7857	Intermediate Similarity	NPC46570
0.7843	Intermediate Similarity	NPC471412
0.7843	Intermediate Similarity	NPC52899
0.7843	Intermediate Similarity	NPC163963
0.7843	Intermediate Similarity	NPC289148
0.7843	Intermediate Similarity	NPC171759
0.7838	Intermediate Similarity	NPC475520
0.7835	Intermediate Similarity	NPC161638
0.783	Intermediate Similarity	NPC475941
0.783	Intermediate Similarity	NPC474901
0.7822	Intermediate Similarity	NPC469986
0.7822	Intermediate Similarity	NPC252295
0.7822	Intermediate Similarity	NPC222011
0.7818	Intermediate Similarity	NPC239273
0.781	Intermediate Similarity	NPC472925
0.7807	Intermediate Similarity	NPC241456
0.7807	Intermediate Similarity	NPC32868
0.78	Intermediate Similarity	NPC329910
0.7798	Intermediate Similarity	NPC470953
0.7789	Intermediate Similarity	NPC64153
0.7788	Intermediate Similarity	NPC189616
0.7788	Intermediate Similarity	NPC269642
0.7788	Intermediate Similarity	NPC96268
0.7788	Intermediate Similarity	NPC107493
0.7778	Intermediate Similarity	NPC470697
0.7778	Intermediate Similarity	NPC475118
0.7778	Intermediate Similarity	NPC148463
0.7767	Intermediate Similarity	NPC148628
0.7767	Intermediate Similarity	NPC214946
0.7767	Intermediate Similarity	NPC88203
0.7767	Intermediate Similarity	NPC162973
0.7767	Intermediate Similarity	NPC76866
0.7767	Intermediate Similarity	NPC246736
0.7767	Intermediate Similarity	NPC304832
0.7767	Intermediate Similarity	NPC286519
0.7757	Intermediate Similarity	NPC197428
0.7755	Intermediate Similarity	NPC191339
0.7755	Intermediate Similarity	NPC286341
0.7748	Intermediate Similarity	NPC473720
0.7748	Intermediate Similarity	NPC153440
0.7748	Intermediate Similarity	NPC475372
0.7745	Intermediate Similarity	NPC287676
0.7745	Intermediate Similarity	NPC469551
0.7745	Intermediate Similarity	NPC476933
0.7736	Intermediate Similarity	NPC476802
0.7736	Intermediate Similarity	NPC89171
0.7732	Intermediate Similarity	NPC474679
0.7723	Intermediate Similarity	NPC69385
0.7723	Intermediate Similarity	NPC108475
0.7723	Intermediate Similarity	NPC110937
0.7723	Intermediate Similarity	NPC170143
0.7723	Intermediate Similarity	NPC213947
0.7719	Intermediate Similarity	NPC472768
0.7714	Intermediate Similarity	NPC295366
0.7708	Intermediate Similarity	NPC175293
0.77	Intermediate Similarity	NPC470232
0.7692	Intermediate Similarity	NPC36321
0.7692	Intermediate Similarity	NPC87927
0.7692	Intermediate Similarity	NPC159442
0.7685	Intermediate Similarity	NPC470960
0.7679	Intermediate Similarity	NPC5292
0.7679	Intermediate Similarity	NPC312536
0.7679	Intermediate Similarity	NPC472667
0.7679	Intermediate Similarity	NPC476960
0.7679	Intermediate Similarity	NPC475041
0.7672	Intermediate Similarity	NPC287423
0.767	Intermediate Similarity	NPC310981
0.767	Intermediate Similarity	NPC472924
0.7664	Intermediate Similarity	NPC474243
0.7658	Intermediate Similarity	NPC472927
0.7658	Intermediate Similarity	NPC476959
0.7653	Intermediate Similarity	NPC152467
0.7647	Intermediate Similarity	NPC78427
0.7647	Intermediate Similarity	NPC474793
0.7647	Intermediate Similarity	NPC471038
0.7647	Intermediate Similarity	NPC16911
0.7636	Intermediate Similarity	NPC238667
0.7632	Intermediate Similarity	NPC170538
0.7624	Intermediate Similarity	NPC111684
0.7624	Intermediate Similarity	NPC29952
0.7624	Intermediate Similarity	NPC58052
0.7624	Intermediate Similarity	NPC307164
0.7619	Intermediate Similarity	NPC98603
0.7615	Intermediate Similarity	NPC475970
0.7611	Intermediate Similarity	NPC4548
0.7611	Intermediate Similarity	NPC476962
0.7611	Intermediate Similarity	NPC474585
0.7611	Intermediate Similarity	NPC476961
0.7611	Intermediate Similarity	NPC79579
0.7604	Intermediate Similarity	NPC469676
0.7604	Intermediate Similarity	NPC474045
0.7604	Intermediate Similarity	NPC261253
0.7604	Intermediate Similarity	NPC220478
0.76	Intermediate Similarity	NPC470385
0.76	Intermediate Similarity	NPC47853
0.76	Intermediate Similarity	NPC224410
0.76	Intermediate Similarity	NPC474841
0.76	Intermediate Similarity	NPC100257
0.76	Intermediate Similarity	NPC473434
0.76	Intermediate Similarity	NPC470386
0.76	Intermediate Similarity	NPC471446
0.7596	Intermediate Similarity	NPC22388
0.7596	Intermediate Similarity	NPC170615
0.7589	Intermediate Similarity	NPC113448
0.7579	Intermediate Similarity	NPC30486
0.7576	Intermediate Similarity	NPC165180
0.7573	Intermediate Similarity	NPC470906
0.7573	Intermediate Similarity	NPC471041
0.7573	Intermediate Similarity	NPC117685
0.7573	Intermediate Similarity	NPC476274
0.7573	Intermediate Similarity	NPC47024
0.7573	Intermediate Similarity	NPC251680
0.757	Intermediate Similarity	NPC275539
0.757	Intermediate Similarity	NPC189075
0.757	Intermediate Similarity	NPC211224
0.757	Intermediate Similarity	NPC61411
0.7568	Intermediate Similarity	NPC148458
0.7568	Intermediate Similarity	NPC176840
0.7568	Intermediate Similarity	NPC470793
0.7568	Intermediate Similarity	NPC196931
0.7568	Intermediate Similarity	NPC476963
0.7565	Intermediate Similarity	NPC55602
0.7565	Intermediate Similarity	NPC11895
0.7565	Intermediate Similarity	NPC469789
0.7549	Intermediate Similarity	NPC96839
0.7549	Intermediate Similarity	NPC38530
0.7549	Intermediate Similarity	NPC474343
0.7549	Intermediate Similarity	NPC47834
0.7549	Intermediate Similarity	NPC253826
0.7549	Intermediate Similarity	NPC84335
0.7547	Intermediate Similarity	NPC37600
0.7547	Intermediate Similarity	NPC278628
0.7547	Intermediate Similarity	NPC470980
0.7547	Intermediate Similarity	NPC231530
0.7547	Intermediate Similarity	NPC469874
0.7547	Intermediate Similarity	NPC475571
0.7545	Intermediate Similarity	NPC962
0.7545	Intermediate Similarity	NPC52634
0.7544	Intermediate Similarity	NPC310511
0.7542	Intermediate Similarity	NPC231529
0.7542	Intermediate Similarity	NPC221414
0.7542	Intermediate Similarity	NPC472770
0.7525	Intermediate Similarity	NPC281134
0.7525	Intermediate Similarity	NPC33473
0.7524	Intermediate Similarity	NPC475526
0.7524	Intermediate Similarity	NPC329345
0.7524	Intermediate Similarity	NPC470310
0.7524	Intermediate Similarity	NPC470954
0.7524	Intermediate Similarity	NPC473283
0.7524	Intermediate Similarity	NPC474775
0.7524	Intermediate Similarity	NPC216114
0.7524	Intermediate Similarity	NPC469985
0.7524	Intermediate Similarity	NPC95899
0.7523	Intermediate Similarity	NPC174471
0.7523	Intermediate Similarity	NPC474871
0.7523	Intermediate Similarity	NPC260786
0.7523	Intermediate Similarity	NPC96739
0.7523	Intermediate Similarity	NPC94650
0.7523	Intermediate Similarity	NPC475495
0.7523	Intermediate Similarity	NPC470281
0.7523	Intermediate Similarity	NPC472928
0.7522	Intermediate Similarity	NPC472933
0.7522	Intermediate Similarity	NPC270850
0.7522	Intermediate Similarity	NPC305260
0.75	Intermediate Similarity	NPC475657
0.75	Intermediate Similarity	NPC79117
0.75	Intermediate Similarity	NPC112457
0.75	Intermediate Similarity	NPC476223

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 NPC118159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1957
0.2-0.3	3853
0.3-0.4	2029
0.4-0.5	673
0.5-0.6	232
0.6-0.7	189
0.7-0.8	25
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
0.7714	Intermediate Similarity	NPD6008	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.73	Intermediate Similarity	NPD5785	Approved
0.7297	Intermediate Similarity	NPD6053	Discontinued
0.7248	Intermediate Similarity	NPD6881	Approved
0.7248	Intermediate Similarity	NPD6899	Approved
0.7245	Intermediate Similarity	NPD5330	Approved
0.7245	Intermediate Similarity	NPD7521	Approved
0.7245	Intermediate Similarity	NPD7334	Approved
0.7245	Intermediate Similarity	NPD6684	Approved
0.7245	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD6409	Approved
0.7222	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD6402	Approved
0.7222	Intermediate Similarity	NPD7128	Approved
0.7222	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7188	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5697	Approved
0.7155	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD5363	Approved
0.7117	Intermediate Similarity	NPD7290	Approved
0.7117	Intermediate Similarity	NPD6883	Approved
0.7117	Intermediate Similarity	NPD7102	Approved
0.7107	Intermediate Similarity	NPD7319	Approved
0.71	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6903	Approved
0.7091	Intermediate Similarity	NPD7320	Approved
0.7091	Intermediate Similarity	NPD6011	Approved
0.708	Intermediate Similarity	NPD4632	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD6847	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD8130	Phase 1
0.7054	Intermediate Similarity	NPD6617	Approved
0.7054	Intermediate Similarity	NPD6869	Approved
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6373	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6372	Approved
0.7019	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD6616	Approved
0.6991	Remote Similarity	NPD8297	Approved
0.6991	Remote Similarity	NPD6882	Approved
0.699	Remote Similarity	NPD5778	Approved
0.699	Remote Similarity	NPD5779	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.697	Remote Similarity	NPD1694	Approved
0.6964	Remote Similarity	NPD6371	Approved
0.6944	Remote Similarity	NPD7632	Discontinued
0.6942	Remote Similarity	NPD7078	Approved
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6009	Approved
0.6893	Remote Similarity	NPD6079	Approved
0.6891	Remote Similarity	NPD6370	Approved
0.6885	Remote Similarity	NPD7736	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.6863	Remote Similarity	NPD1695	Approved
0.6863	Remote Similarity	NPD6673	Approved
0.6863	Remote Similarity	NPD6080	Approved
0.6863	Remote Similarity	NPD5328	Approved
0.6863	Remote Similarity	NPD6904	Approved
0.6837	Remote Similarity	NPD4270	Approved
0.6837	Remote Similarity	NPD4269	Approved
0.6833	Remote Similarity	NPD7604	Phase 2
0.6827	Remote Similarity	NPD6399	Phase 3
0.6814	Remote Similarity	NPD4634	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6807	Remote Similarity	NPD6016	Approved
0.6807	Remote Similarity	NPD6015	Approved
0.6803	Remote Similarity	NPD8293	Discontinued
0.6789	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD5362	Discontinued
0.6759	Remote Similarity	NPD5286	Approved
0.6759	Remote Similarity	NPD5285	Approved
0.6759	Remote Similarity	NPD4696	Approved
0.675	Remote Similarity	NPD5988	Approved
0.6735	Remote Similarity	NPD5369	Approved
0.6731	Remote Similarity	NPD6050	Approved
0.6729	Remote Similarity	NPD6084	Phase 2
0.6729	Remote Similarity	NPD4755	Approved
0.6729	Remote Similarity	NPD6083	Phase 2
0.6721	Remote Similarity	NPD6336	Discontinued
0.6699	Remote Similarity	NPD6051	Approved
0.6698	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5695	Phase 3
0.6697	Remote Similarity	NPD5223	Approved
0.6695	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5225	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6635	Remote Similarity	NPD6698	Approved
0.6635	Remote Similarity	NPD46	Approved
0.6635	Remote Similarity	NPD5692	Phase 3
0.6634	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4252	Approved
0.661	Remote Similarity	NPD6317	Approved
0.6606	Remote Similarity	NPD4700	Approved
0.6606	Remote Similarity	NPD6648	Approved
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6001	Approved
0.6604	Remote Similarity	NPD7900	Approved
0.6604	Remote Similarity	NPD7748	Approved
0.6602	Remote Similarity	NPD5208	Approved
0.6577	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD5174	Approved
0.6574	Remote Similarity	NPD5173	Approved
0.6571	Remote Similarity	NPD8034	Phase 2
0.6571	Remote Similarity	NPD5694	Approved
0.6571	Remote Similarity	NPD8035	Phase 2
0.6571	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD6098	Approved
0.6555	Remote Similarity	NPD6313	Approved
0.6555	Remote Similarity	NPD6314	Approved
0.6545	Remote Similarity	NPD5344	Discontinued
0.6538	Remote Similarity	NPD6101	Approved
0.6538	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6868	Approved
0.6514	Remote Similarity	NPD5696	Approved
0.6509	Remote Similarity	NPD4202	Approved
0.6481	Remote Similarity	NPD4697	Phase 3
0.648	Remote Similarity	NPD6033	Approved
0.6476	Remote Similarity	NPD5207	Approved
0.6471	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD4754	Approved
0.6422	Remote Similarity	NPD7902	Approved
0.6417	Remote Similarity	NPD7328	Approved
0.6417	Remote Similarity	NPD7327	Approved
0.6415	Remote Similarity	NPD7515	Phase 2
0.6415	Remote Similarity	NPD6411	Approved
0.6415	Remote Similarity	NPD7983	Approved
0.6408	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3618	Phase 1
0.6404	Remote Similarity	NPD6412	Phase 2
0.6404	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6908	Approved
0.6393	Remote Similarity	NPD6909	Approved
0.6393	Remote Similarity	NPD8033	Approved
0.6373	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD3665	Phase 1
0.6373	Remote Similarity	NPD4786	Approved
0.6373	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD7516	Approved
0.6348	Remote Similarity	NPD4730	Approved
0.6348	Remote Similarity	NPD4729	Approved
0.6348	Remote Similarity	NPD5128	Approved
0.6346	Remote Similarity	NPD4251	Approved
0.6346	Remote Similarity	NPD4250	Approved
0.6328	Remote Similarity	NPD7260	Phase 2
0.6316	Remote Similarity	NPD4767	Approved
0.6316	Remote Similarity	NPD4768	Approved
0.6311	Remote Similarity	NPD8294	Approved
0.6311	Remote Similarity	NPD8377	Approved
0.63	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6333	Approved
0.6288	Remote Similarity	NPD6334	Approved
0.6275	Remote Similarity	NPD5331	Approved
0.6275	Remote Similarity	NPD5332	Approved
0.6275	Remote Similarity	NPD4788	Approved
0.6275	Remote Similarity	NPD7154	Phase 3
0.6263	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5281	Approved
0.6262	Remote Similarity	NPD5284	Approved
0.626	Remote Similarity	NPD7503	Approved
0.626	Remote Similarity	NPD8380	Approved
0.626	Remote Similarity	NPD8378	Approved
0.626	Remote Similarity	NPD8296	Approved
0.626	Remote Similarity	NPD8335	Approved
0.626	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD4249	Approved
0.6239	Remote Similarity	NPD5248	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