NPASS Compound

Structure

CID156981 OpenBabel06191715522D 34 38 0 0 1 0 0 0 0 0999 V2000 1.8425 4.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4316 3.7831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7366 -2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7867 -2.2961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2365 -0.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 0.3907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4494 0.6075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8221 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4494 -1.5819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 0.4872 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 2.5315 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7965 -0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 -1.3650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 30 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	6.699
LogD:	5.202
LogS:	-4.468
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.326
Synthetic Accessibility Score:	4.681
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.379
MDCK Permeability:	1.5486790289287455e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	96.74445343017578%
Volume Distribution (VD):	0.602
Pgp-substrate:	4.861427307128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.318
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.739
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.34
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	2.683
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.822
Skin Sensitization:	0.072
Carcinogencity:	0.238
Eye Corrosion:	0.913
Eye Irritation:	0.185
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC156981

Natural Product ID:	NPC156981
*Common Name:**	IVNWEUTZHBKHJJ-FUAOEXFOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IVNWEUTZHBKHJJ-FUAOEXFOSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)34-26(3,4)21(27)10-13-29(22,28)7/h8,20-22H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,27-,28+,29+,30-/m0/s1
SMILES:	O=C1CC[C@]2([C@H](C(O1)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631521
PubChem CID:	53326799
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones

*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
NPO7123	Aria intermedia	Species	Rosaceae	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	3
Others	9

Activity Type	# Activity
CELL-LINE	1
Individual Protein	1
Organism	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	14.12	%	PMID[470495]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.32	n.a.	PMID[470496]
NPT24647	CELL-LINE	HepG2 2.2.15	Homo sapiens	CC50	=	477000.0	nM	PMID[470496]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	860.0	nM	PMID[470496]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	360300.0	nM	PMID[470496]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	200.0	n.a.	PMID[470496]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	6.2	%	PMID[470496]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	10.6	%	PMID[470496]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	34.0	%	PMID[470496]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	81.62	%	PMID[470496]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	32700.0	nM	PMID[470496]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	14.5	n.a.	PMID[470496]

☑ 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 NPC156981 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	204
0.1-0.2	1283
0.2-0.3	5678
0.3-0.4	15901
0.4-0.5	7375
0.5-0.6	6449
0.6-0.7	4624
0.7-0.8	1073
0.8-0.85	86
0.85-0.9	17
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC37038
0.9359	High Similarity	NPC231431
0.9241	High Similarity	NPC104545
0.9231	High Similarity	NPC260385
0.9231	High Similarity	NPC280654
0.9231	High Similarity	NPC110094
0.9125	High Similarity	NPC142244
0.9114	High Similarity	NPC199595
0.9103	High Similarity	NPC471897
0.9103	High Similarity	NPC107039
0.9103	High Similarity	NPC471899
0.9036	High Similarity	NPC324063
0.9	High Similarity	NPC477057
0.8987	High Similarity	NPC321514
0.8974	High Similarity	NPC89294
0.8902	High Similarity	NPC200752
0.8889	High Similarity	NPC274050
0.8889	High Similarity	NPC162632
0.8889	High Similarity	NPC221647
0.8889	High Similarity	NPC263272
0.8889	High Similarity	NPC327002
0.8889	High Similarity	NPC471898
0.8889	High Similarity	NPC267691
0.8875	High Similarity	NPC16394
0.8795	High Similarity	NPC96095
0.878	High Similarity	NPC251779
0.878	High Similarity	NPC69101
0.8721	High Similarity	NPC474700
0.8675	High Similarity	NPC70834
0.8659	High Similarity	NPC278459
0.8642	High Similarity	NPC327674
0.8621	High Similarity	NPC120840
0.8621	High Similarity	NPC474728
0.8621	High Similarity	NPC113989
0.8608	High Similarity	NPC192540
0.8608	High Similarity	NPC279666
0.8588	High Similarity	NPC73038
0.8537	High Similarity	NPC267517
0.8523	High Similarity	NPC470590
0.8523	High Similarity	NPC77099
0.8523	High Similarity	NPC60755
0.8523	High Similarity	NPC285184
0.8519	High Similarity	NPC179028
0.8506	High Similarity	NPC30522
0.85	High Similarity	NPC69143
0.8488	Intermediate Similarity	NPC173089
0.8488	Intermediate Similarity	NPC158141
0.8481	Intermediate Similarity	NPC476046
0.8481	Intermediate Similarity	NPC161923
0.8481	Intermediate Similarity	NPC103958
0.8481	Intermediate Similarity	NPC251970
0.8481	Intermediate Similarity	NPC241854
0.8481	Intermediate Similarity	NPC283908
0.8481	Intermediate Similarity	NPC183503
0.8471	Intermediate Similarity	NPC474537
0.8462	Intermediate Similarity	NPC160817
0.8434	Intermediate Similarity	NPC147066
0.8427	Intermediate Similarity	NPC169343
0.8427	Intermediate Similarity	NPC86368
0.8409	Intermediate Similarity	NPC472866
0.8409	Intermediate Similarity	NPC198818
0.8395	Intermediate Similarity	NPC165711
0.8391	Intermediate Similarity	NPC474474
0.8391	Intermediate Similarity	NPC40552
0.8391	Intermediate Similarity	NPC1753
0.8391	Intermediate Similarity	NPC474511
0.8391	Intermediate Similarity	NPC52169
0.8391	Intermediate Similarity	NPC246708
0.8391	Intermediate Similarity	NPC182797
0.8372	Intermediate Similarity	NPC325594
0.8354	Intermediate Similarity	NPC36310
0.8353	Intermediate Similarity	NPC477289
0.8353	Intermediate Similarity	NPC312660
0.8352	Intermediate Similarity	NPC327179
0.8333	Intermediate Similarity	NPC296164
0.8333	Intermediate Similarity	NPC474963
0.8333	Intermediate Similarity	NPC74751
0.8333	Intermediate Similarity	NPC78580
0.8333	Intermediate Similarity	NPC23621
0.8333	Intermediate Similarity	NPC184006
0.8295	Intermediate Similarity	NPC477973
0.8295	Intermediate Similarity	NPC198664
0.8295	Intermediate Similarity	NPC121798
0.8295	Intermediate Similarity	NPC263393
0.8295	Intermediate Similarity	NPC61543
0.8295	Intermediate Similarity	NPC225585
0.8295	Intermediate Similarity	NPC127689
0.8295	Intermediate Similarity	NPC474570
0.8295	Intermediate Similarity	NPC234346
0.8295	Intermediate Similarity	NPC470588
0.8295	Intermediate Similarity	NPC290972
0.8295	Intermediate Similarity	NPC25906
0.8295	Intermediate Similarity	NPC64872
0.8295	Intermediate Similarity	NPC293048
0.8295	Intermediate Similarity	NPC59263
0.8295	Intermediate Similarity	NPC270768
0.8295	Intermediate Similarity	NPC130520
0.8295	Intermediate Similarity	NPC143232
0.8295	Intermediate Similarity	NPC274330
0.8295	Intermediate Similarity	NPC281524
0.8276	Intermediate Similarity	NPC242468
0.8276	Intermediate Similarity	NPC51700
0.8276	Intermediate Similarity	NPC71507
0.8276	Intermediate Similarity	NPC307426
0.8276	Intermediate Similarity	NPC162107
0.8276	Intermediate Similarity	NPC102683
0.8276	Intermediate Similarity	NPC293564
0.8276	Intermediate Similarity	NPC18064
0.8276	Intermediate Similarity	NPC171203
0.8276	Intermediate Similarity	NPC130577
0.8276	Intermediate Similarity	NPC68160
0.8276	Intermediate Similarity	NPC98442
0.8276	Intermediate Similarity	NPC136948
0.8276	Intermediate Similarity	NPC46912
0.8276	Intermediate Similarity	NPC142415
0.8276	Intermediate Similarity	NPC88716
0.8272	Intermediate Similarity	NPC309399
0.8272	Intermediate Similarity	NPC180886
0.8261	Intermediate Similarity	NPC473456
0.8256	Intermediate Similarity	NPC76333
0.825	Intermediate Similarity	NPC166797
0.825	Intermediate Similarity	NPC255168
0.8242	Intermediate Similarity	NPC23241
0.8242	Intermediate Similarity	NPC474727
0.8242	Intermediate Similarity	NPC195715
0.8235	Intermediate Similarity	NPC473592
0.8235	Intermediate Similarity	NPC167103
0.8235	Intermediate Similarity	NPC477373
0.8222	Intermediate Similarity	NPC151722
0.8222	Intermediate Similarity	NPC74855
0.8222	Intermediate Similarity	NPC158059
0.8222	Intermediate Similarity	NPC474436
0.8222	Intermediate Similarity	NPC118490
0.8222	Intermediate Similarity	NPC118519
0.8222	Intermediate Similarity	NPC49776
0.8222	Intermediate Similarity	NPC275809
0.8222	Intermediate Similarity	NPC307335
0.8222	Intermediate Similarity	NPC272075
0.8222	Intermediate Similarity	NPC214756
0.8222	Intermediate Similarity	NPC202728
0.8222	Intermediate Similarity	NPC263780
0.8222	Intermediate Similarity	NPC295643
0.8222	Intermediate Similarity	NPC136313
0.8222	Intermediate Similarity	NPC63118
0.8214	Intermediate Similarity	NPC229584
0.8214	Intermediate Similarity	NPC14203
0.8214	Intermediate Similarity	NPC3915
0.8214	Intermediate Similarity	NPC38350
0.8214	Intermediate Similarity	NPC201912
0.8211	Intermediate Similarity	NPC90177
0.8202	Intermediate Similarity	NPC46441
0.8202	Intermediate Similarity	NPC470589
0.8202	Intermediate Similarity	NPC126369
0.8202	Intermediate Similarity	NPC193750
0.8202	Intermediate Similarity	NPC130278
0.8202	Intermediate Similarity	NPC111110
0.8202	Intermediate Similarity	NPC18872
0.8202	Intermediate Similarity	NPC210037
0.8202	Intermediate Similarity	NPC120968
0.8202	Intermediate Similarity	NPC477872
0.8202	Intermediate Similarity	NPC290614
0.8202	Intermediate Similarity	NPC291028
0.8202	Intermediate Similarity	NPC7260
0.8202	Intermediate Similarity	NPC227467
0.8202	Intermediate Similarity	NPC273621
0.8202	Intermediate Similarity	NPC471896
0.8193	Intermediate Similarity	NPC215843
0.8193	Intermediate Similarity	NPC477371
0.8182	Intermediate Similarity	NPC181225
0.8182	Intermediate Similarity	NPC473242
0.8182	Intermediate Similarity	NPC470629
0.8182	Intermediate Similarity	NPC474512
0.8182	Intermediate Similarity	NPC290690
0.8182	Intermediate Similarity	NPC17733
0.8171	Intermediate Similarity	NPC472300
0.8171	Intermediate Similarity	NPC66105
0.8161	Intermediate Similarity	NPC262085
0.8161	Intermediate Similarity	NPC10005
0.8161	Intermediate Similarity	NPC322159
0.8161	Intermediate Similarity	NPC329943
0.8161	Intermediate Similarity	NPC91525
0.8161	Intermediate Similarity	NPC9892
0.8161	Intermediate Similarity	NPC72638
0.8152	Intermediate Similarity	NPC230151
0.8148	Intermediate Similarity	NPC476844
0.8148	Intermediate Similarity	NPC201027
0.8132	Intermediate Similarity	NPC114159
0.8132	Intermediate Similarity	NPC6818
0.8132	Intermediate Similarity	NPC91010
0.8132	Intermediate Similarity	NPC191412
0.8132	Intermediate Similarity	NPC148964
0.8118	Intermediate Similarity	NPC133391
0.8118	Intermediate Similarity	NPC320514
0.8118	Intermediate Similarity	NPC310989
0.8118	Intermediate Similarity	NPC260956
0.8111	Intermediate Similarity	NPC25299
0.8111	Intermediate Similarity	NPC282616
0.8111	Intermediate Similarity	NPC84319
0.8111	Intermediate Similarity	NPC145067
0.8111	Intermediate Similarity	NPC38754

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 NPC156981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1625
0.2-0.3	4016
0.3-0.4	2241
0.4-0.5	642
0.5-0.6	222
0.6-0.7	174
0.7-0.8	45
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7748	Approved
0.8111	Intermediate Similarity	NPD7515	Phase 2
0.809	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7902	Approved
0.8022	Intermediate Similarity	NPD6399	Phase 3
0.7978	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6098	Approved
0.7889	Intermediate Similarity	NPD6080	Approved
0.7889	Intermediate Similarity	NPD6904	Approved
0.7889	Intermediate Similarity	NPD6673	Approved
0.7872	Intermediate Similarity	NPD6084	Phase 2
0.7872	Intermediate Similarity	NPD6083	Phase 2
0.7865	Intermediate Similarity	NPD3573	Approved
0.7778	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD5737	Approved
0.7753	Intermediate Similarity	NPD7146	Approved
0.7753	Intermediate Similarity	NPD7334	Approved
0.7753	Intermediate Similarity	NPD7521	Approved
0.7753	Intermediate Similarity	NPD6409	Approved
0.7753	Intermediate Similarity	NPD6684	Approved
0.7753	Intermediate Similarity	NPD5330	Approved
0.7742	Intermediate Similarity	NPD7900	Approved
0.7742	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4221	Approved
0.7701	Intermediate Similarity	NPD4223	Phase 3
0.7674	Intermediate Similarity	NPD4695	Discontinued
0.766	Intermediate Similarity	NPD5695	Phase 3
0.764	Intermediate Similarity	NPD5329	Approved
0.7604	Intermediate Similarity	NPD5696	Approved
0.7582	Intermediate Similarity	NPD5208	Approved
0.7582	Intermediate Similarity	NPD6903	Approved
0.7579	Intermediate Similarity	NPD7614	Phase 1
0.7528	Intermediate Similarity	NPD4197	Approved
0.7528	Intermediate Similarity	NPD4786	Approved
0.7527	Intermediate Similarity	NPD8034	Phase 2
0.7527	Intermediate Similarity	NPD6050	Approved
0.7527	Intermediate Similarity	NPD5693	Phase 1
0.7527	Intermediate Similarity	NPD5281	Approved
0.7527	Intermediate Similarity	NPD5284	Approved
0.7527	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD3667	Approved
0.7474	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5692	Phase 3
0.7363	Intermediate Similarity	NPD4690	Approved
0.7363	Intermediate Similarity	NPD4623	Approved
0.7363	Intermediate Similarity	NPD5205	Approved
0.7363	Intermediate Similarity	NPD4519	Discontinued
0.7363	Intermediate Similarity	NPD4693	Phase 3
0.7363	Intermediate Similarity	NPD4689	Approved
0.7363	Intermediate Similarity	NPD4138	Approved
0.7363	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4688	Approved
0.734	Intermediate Similarity	NPD6411	Approved
0.734	Intermediate Similarity	NPD5694	Approved
0.7333	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD3666	Approved
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7327	Intermediate Similarity	NPD6402	Approved
0.7327	Intermediate Similarity	NPD7128	Approved
0.7327	Intermediate Similarity	NPD5739	Approved
0.7327	Intermediate Similarity	NPD6675	Approved
0.7312	Intermediate Similarity	NPD4753	Phase 2
0.7303	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7638	Approved
0.7241	Intermediate Similarity	NPD3617	Approved
0.7234	Intermediate Similarity	NPD5207	Approved
0.7216	Intermediate Similarity	NPD7732	Phase 3
0.7188	Intermediate Similarity	NPD6001	Approved
0.7184	Intermediate Similarity	NPD7320	Approved
0.7184	Intermediate Similarity	NPD6881	Approved
0.7184	Intermediate Similarity	NPD6899	Approved
0.7174	Intermediate Similarity	NPD5690	Phase 2
0.7174	Intermediate Similarity	NPD3618	Phase 1
0.7174	Intermediate Similarity	NPD4694	Approved
0.7174	Intermediate Similarity	NPD5280	Approved
0.7172	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7640	Approved
0.7159	Intermediate Similarity	NPD7645	Phase 2
0.7143	Intermediate Similarity	NPD3668	Phase 3
0.7143	Intermediate Similarity	NPD4243	Approved
0.7128	Intermediate Similarity	NPD5328	Approved
0.7128	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6101	Approved
0.7115	Intermediate Similarity	NPD6373	Approved
0.7115	Intermediate Similarity	NPD6372	Approved
0.7087	Intermediate Similarity	NPD5697	Approved
0.7087	Intermediate Similarity	NPD5701	Approved
0.7048	Intermediate Similarity	NPD7290	Approved
0.7048	Intermediate Similarity	NPD7102	Approved
0.7048	Intermediate Similarity	NPD6883	Approved
0.7033	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.6981	Remote Similarity	NPD6617	Approved
0.6981	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6869	Approved
0.6981	Remote Similarity	NPD6847	Approved
0.6981	Remote Similarity	NPD8130	Phase 1
0.6981	Remote Similarity	NPD6650	Approved
0.6981	Remote Similarity	NPD6649	Approved
0.6979	Remote Similarity	NPD6079	Approved
0.6977	Remote Similarity	NPD4784	Approved
0.6977	Remote Similarity	NPD4785	Approved
0.6966	Remote Similarity	NPD4195	Approved
0.6961	Remote Similarity	NPD6052	Approved
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6014	Approved
0.6951	Remote Similarity	NPD4224	Phase 2
0.6947	Remote Similarity	NPD6051	Approved
0.6941	Remote Similarity	NPD6081	Approved
0.6939	Remote Similarity	NPD5654	Approved
0.6939	Remote Similarity	NPD4629	Approved
0.6939	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD6412	Phase 2
0.6916	Remote Similarity	NPD8297	Approved
0.6916	Remote Similarity	NPD6882	Approved
0.6907	Remote Similarity	NPD4202	Approved
0.6905	Remote Similarity	NPD4137	Phase 3
0.6889	Remote Similarity	NPD7525	Registered
0.6824	Remote Similarity	NPD4691	Approved
0.6824	Remote Similarity	NPD4747	Approved
0.6818	Remote Similarity	NPD7115	Discovery
0.6809	Remote Similarity	NPD5279	Phase 3
0.68	Remote Similarity	NPD5959	Approved
0.68	Remote Similarity	NPD4755	Approved
0.6786	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6614	Approved
0.6747	Remote Similarity	NPD7331	Phase 2
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6705	Remote Similarity	NPD3702	Approved
0.6705	Remote Similarity	NPD7339	Approved
0.6705	Remote Similarity	NPD8039	Approved
0.6705	Remote Similarity	NPD5275	Approved
0.6705	Remote Similarity	NPD4190	Phase 3
0.6705	Remote Similarity	NPD6942	Approved
0.6701	Remote Similarity	NPD4096	Approved
0.67	Remote Similarity	NPD5222	Approved
0.67	Remote Similarity	NPD5221	Approved
0.67	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4697	Phase 3
0.6698	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5173	Approved
0.6629	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6117	Approved
0.6627	Remote Similarity	NPD7341	Phase 2
0.6607	Remote Similarity	NPD6335	Approved
0.6606	Remote Similarity	NPD6053	Discontinued
0.6602	Remote Similarity	NPD5223	Approved
0.6591	Remote Similarity	NPD4058	Approved
0.6591	Remote Similarity	NPD5733	Approved
0.6591	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5360	Phase 3
0.6577	Remote Similarity	NPD6868	Approved
0.6577	Remote Similarity	NPD6274	Approved
0.6566	Remote Similarity	NPD5133	Approved
0.6556	Remote Similarity	NPD6116	Phase 1
0.6552	Remote Similarity	NPD5777	Approved
0.6549	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD7101	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD5091	Approved
0.6538	Remote Similarity	NPD5211	Phase 2
0.6538	Remote Similarity	NPD5224	Approved
0.6538	Remote Similarity	NPD5226	Approved
0.6538	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD4633	Approved
0.6538	Remote Similarity	NPD7632	Discontinued
0.6526	Remote Similarity	NPD1694	Approved
0.6518	Remote Similarity	NPD6317	Approved
0.65	Remote Similarity	NPD5707	Approved
0.6495	Remote Similarity	NPD4518	Approved
0.6484	Remote Similarity	NPD6697	Approved
0.6484	Remote Similarity	NPD6115	Approved
0.6484	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6114	Approved
0.6484	Remote Similarity	NPD6118	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4754	Approved
0.6476	Remote Similarity	NPD5174	Approved
0.6476	Remote Similarity	NPD5175	Approved
0.6466	Remote Similarity	NPD8328	Phase 3
0.6465	Remote Similarity	NPD7637	Suspended
0.646	Remote Similarity	NPD6314	Approved
0.646	Remote Similarity	NPD6313	Approved
0.6452	Remote Similarity	NPD5369	Approved
0.6452	Remote Similarity	NPD8028	Phase 2
0.6435	Remote Similarity	NPD6909	Approved
0.6435	Remote Similarity	NPD6908	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