NPASS Compound

Structure

NPC48949 OpenBabel07101718332D 45 47 0 0 1 0 0 0 0 0999 V2000 -0.7798 4.0177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8577 3.5789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2382 3.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0858 1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4166 -4.8106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1730 -4.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8946 0.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1791 -1.1785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0566 0.8639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2864 2.1269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3410 2.3802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1321 -3.1394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5896 -0.5893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5397 1.1815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5074 -2.3859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9649 0.1642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 -1.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7348 -0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 -0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0877 3.3256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2382 2.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7919 -4.0571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5544 -0.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0396 -0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 0.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 -1.6708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7348 -1.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 -0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 0.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4007 -0.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7209 0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 2 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 -3.8872 1.2655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 -2.6495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5825 -1.6708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 1.2655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3118 -1.3126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8668 1.1902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 25 1 0 0 0 0 9 36 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 22 2 0 0 0 0 12 13 1 0 0 0 0 12 23 2 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 24 2 0 0 0 0 15 18 1 0 0 0 0 15 25 2 0 0 0 0 16 36 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 37 1 0 0 0 0 26 36 1 1 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 39 1 0 0 0 0 29 30 2 0 0 0 0 29 40 1 0 0 0 0 30 41 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 31 34 1 0 0 0 0 32 42 2 0 0 0 0 33 37 1 0 0 0 0 33 43 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 35 37 1 0 0 0 0 35 38 1 0 0 0 0 35 45 2 0 0 0 0 36 38 1 6 0 0 0 37 17 1 6 0 0 0 38 18 1 6 0 0 0 M END

Physi-Chem Properties

Molecular Weight:	618.36
Volume:	672.665
LogP:	8.227
LogD:	5.265
LogS:	-3.672
# Rotatable Bonds:	11
TPSA:	128.97
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.075
Synthetic Accessibility Score:	5.834
Fsp3:	0.526
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.134
MDCK Permeability:	1.3145894627086818e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.772
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	94.23719024658203%
Volume Distribution (VD):	1.923
Pgp-substrate:	7.641294002532959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.807
CYP2C19-substrate:	0.347
CYP2C9-inhibitor:	0.613
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.918
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.772

ADMET: Excretion

Clearance (CL):	21.442
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.702
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.261
Skin Sensitization:	0.031
Carcinogencity:	0.401
Eye Corrosion:	0.015
Eye Irritation:	0.576
Respiratory Toxicity:	0.806

Download Data

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

Natural Product: NPC48949

Natural Product ID:	NPC48949
*Common Name:**	Guttiferone L
IUPAC Name:	n.a.
Synonyms:	16-Hydroxyguttiferone K
Standard InCHIKey:	FERVNTMHOSAJOS-HYOCDBLYSA-N
Standard InCHI:	InChI=1S/C38H50O7/c1-22(2)11-10-16-36(9)26(13-12-23(3)4)21-37(17-14-24(5)6)33(43)31(32(42)27-19-29(40)30(41)20-28(27)39)34(44)38(36,35(37)45)18-15-25(7)8/h11-12,14-15,19-20,26,39-41,43H,10,13,16-18,21H2,1-9H3/t26-,36+,37+,38-/m1/s1
SMILES:	CC(=CCC[C@@]1(C)[C@H](CC=C(C)C)C[C@@]2(CC=C(C)C)C(=C(C(=O)c3cc(c(cc3O)O)O)C(=O)[C@]1(CC=C(C)C)C2=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387644
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO17459	Rheedia calcicola	Species	Clusiaceae	Eukaryota	n.a.	Madagascar rain forest	n.a.	PMID[17348706]
NPO17459	Rheedia calcicola	Species	Clusiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[571141]

☑ 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 NPC48949 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	426
0.1-0.2	1590
0.2-0.3	3351
0.3-0.4	8776
0.4-0.5	10454
0.5-0.6	5358
0.6-0.7	7112
0.7-0.8	5315
0.8-0.85	257
0.85-0.9	39
0.9-0.95	18
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9108	High Similarity	NPC470377
0.9108	High Similarity	NPC478059
0.9108	High Similarity	NPC478060
0.9108	High Similarity	NPC471975
0.9108	High Similarity	NPC470374
0.9028	High Similarity	NPC91887
0.9028	High Similarity	NPC473779
0.9028	High Similarity	NPC297797
0.9028	High Similarity	NPC245760
0.9028	High Similarity	NPC23667
0.9028	High Similarity	NPC114333
0.9028	High Similarity	NPC46242
0.9028	High Similarity	NPC28592
0.9028	High Similarity	NPC165191
0.9028	High Similarity	NPC289358
0.9028	High Similarity	NPC50615
0.9028	High Similarity	NPC469857
0.9028	High Similarity	NPC5014
0.9028	High Similarity	NPC157284
0.9028	High Similarity	NPC477849
0.9028	High Similarity	NPC51531
0.9028	High Similarity	NPC149773
0.9028	High Similarity	NPC473479
0.9028	High Similarity	NPC42384
0.8966	High Similarity	NPC294330
0.8926	High Similarity	NPC476535
0.8912	High Similarity	NPC291078
0.8904	High Similarity	NPC473527
0.8889	High Similarity	NPC7464
0.8882	High Similarity	NPC471969
0.8851	High Similarity	NPC238629
0.8844	High Similarity	NPC92079
0.8816	High Similarity	NPC474191
0.8784	High Similarity	NPC471972
0.8784	High Similarity	NPC471971
0.8784	High Similarity	NPC469855
0.8784	High Similarity	NPC30846
0.8707	High Similarity	NPC472903
0.8699	High Similarity	NPC290030
0.8693	High Similarity	NPC476532
0.8667	High Similarity	NPC8493
0.8667	High Similarity	NPC144247
0.8667	High Similarity	NPC294679
0.8667	High Similarity	NPC469856
0.8667	High Similarity	NPC469375
0.8667	High Similarity	NPC469854
0.8667	High Similarity	NPC145301
0.8649	High Similarity	NPC203063
0.8645	High Similarity	NPC477048
0.8645	High Similarity	NPC477047
0.8639	High Similarity	NPC123714
0.8639	High Similarity	NPC471974
0.8639	High Similarity	NPC469680
0.8639	High Similarity	NPC469681
0.863	High Similarity	NPC65005
0.863	High Similarity	NPC264112
0.863	High Similarity	NPC194764
0.8591	High Similarity	NPC472904
0.8581	High Similarity	NPC476533
0.8562	High Similarity	NPC471907
0.8553	High Similarity	NPC471970
0.8535	High Similarity	NPC470762
0.8535	High Similarity	NPC474167
0.8533	High Similarity	NPC193555
0.8516	High Similarity	NPC35
0.8514	High Similarity	NPC230811
0.8514	High Similarity	NPC87723
0.85	High Similarity	NPC470694
0.8497	Intermediate Similarity	NPC10842
0.8493	Intermediate Similarity	NPC475088
0.8483	Intermediate Similarity	NPC175738
0.8483	Intermediate Similarity	NPC135801
0.8471	Intermediate Similarity	NPC472048
0.8456	Intermediate Similarity	NPC143438
0.8446	Intermediate Similarity	NPC53001
0.8446	Intermediate Similarity	NPC147418
0.8442	Intermediate Similarity	NPC264229
0.8442	Intermediate Similarity	NPC132810
0.8442	Intermediate Similarity	NPC46549
0.8438	Intermediate Similarity	NPC278427
0.8438	Intermediate Similarity	NPC472275
0.8435	Intermediate Similarity	NPC129752
0.8435	Intermediate Similarity	NPC14377
0.8428	Intermediate Similarity	NPC172770
0.8428	Intermediate Similarity	NPC185258
0.8425	Intermediate Similarity	NPC138472
0.8425	Intermediate Similarity	NPC4170
0.8414	Intermediate Similarity	NPC469526
0.8414	Intermediate Similarity	NPC34070
0.8403	Intermediate Similarity	NPC25736
0.84	Intermediate Similarity	NPC169452
0.84	Intermediate Similarity	NPC181560
0.84	Intermediate Similarity	NPC471853
0.8389	Intermediate Similarity	NPC473622
0.8387	Intermediate Similarity	NPC237441
0.8378	Intermediate Similarity	NPC191976
0.8375	Intermediate Similarity	NPC119224
0.8375	Intermediate Similarity	NPC235018
0.8375	Intermediate Similarity	NPC45146
0.8367	Intermediate Similarity	NPC282780
0.8367	Intermediate Similarity	NPC166480
0.8366	Intermediate Similarity	NPC258856
0.8365	Intermediate Similarity	NPC179732
0.8365	Intermediate Similarity	NPC236796
0.8365	Intermediate Similarity	NPC79053
0.8345	Intermediate Similarity	NPC26697
0.8345	Intermediate Similarity	NPC244441
0.8345	Intermediate Similarity	NPC233056
0.8333	Intermediate Similarity	NPC138099
0.8333	Intermediate Similarity	NPC242994
0.8323	Intermediate Similarity	NPC32694
0.8322	Intermediate Similarity	NPC277559
0.8322	Intermediate Similarity	NPC471905
0.8313	Intermediate Similarity	NPC197856
0.8312	Intermediate Similarity	NPC273798
0.8312	Intermediate Similarity	NPC271944
0.8312	Intermediate Similarity	NPC110882
0.8312	Intermediate Similarity	NPC85393
0.8311	Intermediate Similarity	NPC249272
0.8302	Intermediate Similarity	NPC142339
0.8301	Intermediate Similarity	NPC244691
0.8299	Intermediate Similarity	NPC111845
0.8291	Intermediate Similarity	NPC127172
0.8291	Intermediate Similarity	NPC476631
0.8291	Intermediate Similarity	NPC89474
0.8289	Intermediate Similarity	NPC474961
0.828	Intermediate Similarity	NPC221249
0.8274	Intermediate Similarity	NPC23553
0.8274	Intermediate Similarity	NPC77179
0.8267	Intermediate Similarity	NPC416
0.8267	Intermediate Similarity	NPC61398
0.8261	Intermediate Similarity	NPC161947
0.8261	Intermediate Similarity	NPC155302
0.8261	Intermediate Similarity	NPC84571
0.8261	Intermediate Similarity	NPC320359
0.8261	Intermediate Similarity	NPC80375
0.8255	Intermediate Similarity	NPC254847
0.8255	Intermediate Similarity	NPC223836
0.8247	Intermediate Similarity	NPC75295
0.8247	Intermediate Similarity	NPC12402
0.8243	Intermediate Similarity	NPC44437
0.8243	Intermediate Similarity	NPC12070
0.8243	Intermediate Similarity	NPC270899
0.8239	Intermediate Similarity	NPC234485
0.8239	Intermediate Similarity	NPC130589
0.8239	Intermediate Similarity	NPC113906
0.8239	Intermediate Similarity	NPC134287
0.8235	Intermediate Similarity	NPC246153
0.8228	Intermediate Similarity	NPC470340
0.8228	Intermediate Similarity	NPC249570
0.8228	Intermediate Similarity	NPC161778
0.8224	Intermediate Similarity	NPC290550
0.8221	Intermediate Similarity	NPC329669
0.8221	Intermediate Similarity	NPC236132
0.8221	Intermediate Similarity	NPC101769
0.8221	Intermediate Similarity	NPC220313
0.8221	Intermediate Similarity	NPC472278
0.8221	Intermediate Similarity	NPC473313
0.8219	Intermediate Similarity	NPC117609
0.8219	Intermediate Similarity	NPC259942
0.8217	Intermediate Similarity	NPC10467
0.8217	Intermediate Similarity	NPC280295
0.8212	Intermediate Similarity	NPC162939
0.821	Intermediate Similarity	NPC278052
0.821	Intermediate Similarity	NPC258331
0.821	Intermediate Similarity	NPC266365
0.821	Intermediate Similarity	NPC40491
0.821	Intermediate Similarity	NPC311740
0.821	Intermediate Similarity	NPC87431
0.82	Intermediate Similarity	NPC53206
0.82	Intermediate Similarity	NPC49911
0.82	Intermediate Similarity	NPC53414
0.8199	Intermediate Similarity	NPC100123
0.8199	Intermediate Similarity	NPC46736
0.8194	Intermediate Similarity	NPC143685
0.8194	Intermediate Similarity	NPC473691
0.8188	Intermediate Similarity	NPC72918
0.8188	Intermediate Similarity	NPC290803
0.8187	Intermediate Similarity	NPC274730
0.8187	Intermediate Similarity	NPC138243
0.8187	Intermediate Similarity	NPC471968
0.8182	Intermediate Similarity	NPC126204
0.8182	Intermediate Similarity	NPC107009
0.8176	Intermediate Similarity	NPC294226
0.8176	Intermediate Similarity	NPC472211
0.8176	Intermediate Similarity	NPC267205
0.8176	Intermediate Similarity	NPC114183
0.8176	Intermediate Similarity	NPC107109
0.8176	Intermediate Similarity	NPC305710
0.8176	Intermediate Similarity	NPC124714
0.8176	Intermediate Similarity	NPC250557
0.8176	Intermediate Similarity	NPC93552
0.8176	Intermediate Similarity	NPC273248
0.8171	Intermediate Similarity	NPC156432
0.8171	Intermediate Similarity	NPC473286
0.817	Intermediate Similarity	NPC135524
0.817	Intermediate Similarity	NPC248068
0.8166	Intermediate Similarity	NPC221820
0.8165	Intermediate Similarity	NPC19980
0.8165	Intermediate Similarity	NPC202157

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 NPC48949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	959
0.2-0.3	1762
0.3-0.4	2972
0.4-0.5	1935
0.5-0.6	816
0.6-0.7	260
0.7-0.8	62
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
0.8483	Intermediate Similarity	NPD943	Approved
0.8255	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2801	Approved
0.7949	Intermediate Similarity	NPD7390	Discontinued
0.784	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7473	Discontinued
0.7785	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1511	Approved
0.7671	Intermediate Similarity	NPD9269	Phase 2
0.7669	Intermediate Similarity	NPD1934	Approved
0.7635	Intermediate Similarity	NPD1470	Approved
0.7625	Intermediate Similarity	NPD1512	Approved
0.7619	Intermediate Similarity	NPD6232	Discontinued
0.7547	Intermediate Similarity	NPD3300	Phase 2
0.7532	Intermediate Similarity	NPD8166	Discontinued
0.753	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD1201	Approved
0.747	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2800	Approved
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7419	Intermediate Similarity	NPD6651	Approved
0.741	Intermediate Similarity	NPD7819	Suspended
0.7397	Intermediate Similarity	NPD9268	Approved
0.7389	Intermediate Similarity	NPD5406	Approved
0.7389	Intermediate Similarity	NPD5405	Approved
0.7389	Intermediate Similarity	NPD5404	Approved
0.7389	Intermediate Similarity	NPD5408	Approved
0.7346	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3818	Discontinued
0.7333	Intermediate Similarity	NPD4380	Phase 2
0.7326	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6166	Phase 2
0.7326	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1510	Phase 2
0.7321	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1607	Approved
0.7296	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1240	Approved
0.7278	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7278	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6099	Approved
0.7257	Intermediate Similarity	NPD7074	Phase 3
0.7239	Intermediate Similarity	NPD2532	Approved
0.7239	Intermediate Similarity	NPD2534	Approved
0.7239	Intermediate Similarity	NPD2533	Approved
0.723	Intermediate Similarity	NPD2932	Approved
0.7215	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1465	Phase 2
0.72	Intermediate Similarity	NPD5844	Phase 1
0.72	Intermediate Similarity	NPD7054	Approved
0.7192	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7075	Discontinued
0.7167	Intermediate Similarity	NPD8150	Discontinued
0.7162	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7159	Intermediate Similarity	NPD7472	Approved
0.7151	Intermediate Similarity	NPD6959	Discontinued
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6599	Discontinued
0.7114	Intermediate Similarity	NPD3019	Approved
0.7101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7411	Suspended
0.7081	Intermediate Similarity	NPD1549	Phase 2
0.7079	Intermediate Similarity	NPD7251	Discontinued
0.7072	Intermediate Similarity	NPD8434	Phase 2
0.7066	Intermediate Similarity	NPD3226	Approved
0.7052	Intermediate Similarity	NPD1247	Approved
0.7039	Intermediate Similarity	NPD7808	Phase 3
0.7029	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6797	Phase 2
0.7019	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2796	Approved
0.6951	Remote Similarity	NPD6190	Approved
0.6948	Remote Similarity	NPD1164	Approved
0.6944	Remote Similarity	NPD4750	Phase 3
0.6936	Remote Similarity	NPD6234	Discontinued
0.6931	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7768	Phase 2
0.691	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3749	Approved
0.6875	Remote Similarity	NPD3926	Phase 2
0.6867	Remote Similarity	NPD6799	Approved
0.686	Remote Similarity	NPD5402	Approved
0.6851	Remote Similarity	NPD5032	Approved
0.6842	Remote Similarity	NPD6801	Discontinued
0.6842	Remote Similarity	NPD37	Approved
0.6828	Remote Similarity	NPD3022	Approved
0.6828	Remote Similarity	NPD3021	Approved
0.6813	Remote Similarity	NPD5035	Approved
0.681	Remote Similarity	NPD2346	Discontinued
0.681	Remote Similarity	NPD2344	Approved
0.6796	Remote Similarity	NPD5031	Approved
0.6796	Remote Similarity	NPD6559	Discontinued
0.6796	Remote Similarity	NPD5027	Approved
0.6796	Remote Similarity	NPD5029	Approved
0.679	Remote Similarity	NPD2799	Discontinued
0.6765	Remote Similarity	NPD7458	Discontinued
0.6763	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7228	Approved
0.6758	Remote Similarity	NPD4954	Approved
0.6758	Remote Similarity	NPD36	Approved
0.6758	Remote Similarity	NPD4955	Approved
0.6758	Remote Similarity	NPD5034	Approved
0.6758	Remote Similarity	NPD5028	Approved
0.6758	Remote Similarity	NPD5026	Approved
0.6746	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7700	Phase 2
0.6737	Remote Similarity	NPD7699	Phase 2
0.6732	Remote Similarity	NPD3023	Approved
0.6732	Remote Similarity	NPD3026	Approved
0.6727	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4966	Approved
0.6724	Remote Similarity	NPD4965	Approved
0.6724	Remote Similarity	NPD4967	Phase 2
0.6723	Remote Similarity	NPD5711	Approved
0.6723	Remote Similarity	NPD5710	Approved
0.6722	Remote Similarity	NPD6020	Phase 2
0.6711	Remote Similarity	NPD3024	Approved
0.6711	Remote Similarity	NPD3025	Approved
0.6708	Remote Similarity	NPD447	Suspended
0.6703	Remote Similarity	NPD5030	Phase 2
0.6703	Remote Similarity	NPD5037	Approved
0.6703	Remote Similarity	NPD5038	Approved
0.6688	Remote Similarity	NPD2798	Approved
0.6687	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4628	Phase 3
0.6687	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD6534	Approved
0.665	Remote Similarity	NPD8151	Discontinued
0.6649	Remote Similarity	NPD5036	Approved
0.6647	Remote Similarity	NPD2309	Approved
0.6646	Remote Similarity	NPD9494	Approved
0.6646	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3972	Approved
0.6631	Remote Similarity	NPD6836	Approved
0.663	Remote Similarity	NPD8312	Approved
0.663	Remote Similarity	NPD8313	Approved
0.6625	Remote Similarity	NPD3764	Approved
0.6624	Remote Similarity	NPD3094	Phase 2
0.6611	Remote Similarity	NPD5033	Approved
0.6606	Remote Similarity	NPD1471	Phase 3
0.6604	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7003	Approved
0.6584	Remote Similarity	NPD6663	Approved
0.6582	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6781	Approved
0.658	Remote Similarity	NPD6778	Approved
0.658	Remote Similarity	NPD6780	Approved
0.658	Remote Similarity	NPD6777	Approved
0.658	Remote Similarity	NPD6779	Approved
0.658	Remote Similarity	NPD6782	Approved
0.658	Remote Similarity	NPD6776	Approved
0.6577	Remote Similarity	NPD7635	Approved
0.6575	Remote Similarity	NPD3751	Discontinued
0.6573	Remote Similarity	NPD8127	Discontinued
0.6564	Remote Similarity	NPD7698	Approved
0.6564	Remote Similarity	NPD7696	Phase 3
0.6564	Remote Similarity	NPD7697	Approved
0.6564	Remote Similarity	NPD7435	Discontinued
0.6562	Remote Similarity	NPD3027	Phase 3
0.6556	Remote Similarity	NPD2403	Approved
0.6554	Remote Similarity	NPD919	Approved
0.6545	Remote Similarity	NPD1551	Phase 2
0.6541	Remote Similarity	NPD5736	Approved
0.6541	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7286	Phase 2
0.6531	Remote Similarity	NPD8319	Approved
0.6531	Remote Similarity	NPD9266	Approved
0.6531	Remote Similarity	NPD74	Approved
0.6531	Remote Similarity	NPD7870	Phase 2
0.6531	Remote Similarity	NPD7871	Phase 2
0.6531	Remote Similarity	NPD8320	Phase 1
0.6527	Remote Similarity	NPD1243	Approved
0.6522	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3268	Approved
0.6522	Remote Similarity	NPD2313	Discontinued
0.6522	Remote Similarity	NPD5039	Approved
0.6522	Remote Similarity	NPD7685	Pre-registration
0.6522	Remote Similarity	NPD8368	Discontinued
0.6515	Remote Similarity	NPD7701	Phase 2
0.6514	Remote Similarity	NPD5761	Phase 2
0.6514	Remote Similarity	NPD5760	Phase 2
0.6513	Remote Similarity	NPD9493	Approved
0.65	Remote Similarity	NPD7801	Approved
0.6486	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7199	Phase 2
0.6474	Remote Similarity	NPD5968	Phase 3

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