NPASS Compound

Structure

NPC134197 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 3.1093 -1.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7154 -0.9438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3319 -2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5681 -3.9956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6181 -2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3569 -2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0335 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7617 -0.7411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4604 0.1862 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6887 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4604 1.7638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1056 -3.1512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1366 2.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 0.4875 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 2.5331 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7617 2.6911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6181 -3.9956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7096 3.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1669 2.4551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0806 -3.1512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 4 19 1 0 0 0 0 6 29 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 19 21 1 0 0 0 0 20 18 1 1 0 0 0 20 26 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 29 1 1 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 31 1 1 0 0 0 24 32 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 31 1 6 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 31 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	543.911
LogP:	5.025
LogD:	4.593
LogS:	-4.406
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	5.118
Fsp3:	0.806
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.385
MDCK Permeability:	1.24162597785471e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.398

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	80.41704559326172%
Volume Distribution (VD):	0.57
Pgp-substrate:	14.85413646697998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.581
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	4.459
Half-life (T1/2):	0.522

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.449
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.341
Skin Sensitization:	0.587
Carcinogencity:	0.113
Eye Corrosion:	0.095
Eye Irritation:	0.03
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC134197

Natural Product ID:	NPC134197
*Common Name:**	Acanthosessiligenin I
IUPAC Name:	(3S,4S,5R,8R,9R,10R,13S,14R,15R,17S)-17-hydroxy-4-(3-methoxy-3-oxopropyl)-4,9,10-trimethyl-3,15-bis(prop-1-en-2-yl)-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms:	Acanthosessiligenin I
Standard InCHIKey:	NLQYJKRUOHDYPF-FZJIDXKTSA-N
Standard InCHI:	InChI=1S/C31H48O5/c1-18(2)20-17-24(32)31(27(34)35)16-15-29(6)22(26(20)31)9-10-23-28(5,13-12-25(33)36-8)21(19(3)4)11-14-30(23,29)7/h20-24,26,32H,1,3,9-17H2,2,4-8H3,(H,34,35)/t20-,21-,22+,23+,24-,26+,28-,29+,30+,31+/m0/s1
SMILES:	COC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@]2([C@@H]1[C@@H](C[C@@H]2O)C(=C)C)C(=O)O)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063154
PubChem CID:	60154970
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	Fruits	n.a.	n.a.	PMID[22691179]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8
Others	1

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	10000.0	nM	PMID[543613]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[543613]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	<	10000.0	nM	PMID[543613]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[543613]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[543613]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[543613]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	<	10000.0	nM	PMID[543613]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	11300.0	nM	PMID[543613]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	88.8	%	PMID[543613]

☑ 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 NPC134197 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	187
0.1-0.2	1538
0.2-0.3	6429
0.3-0.4	15469
0.4-0.5	5899
0.5-0.6	5554
0.6-0.7	5322
0.7-0.8	1994
0.8-0.85	244
0.85-0.9	48
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC211162
0.9639	High Similarity	NPC183374
0.9398	High Similarity	NPC80590
0.9294	High Similarity	NPC24772
0.9294	High Similarity	NPC116146
0.9268	High Similarity	NPC245866
0.9205	High Similarity	NPC205173
0.9157	High Similarity	NPC263974
0.907	High Similarity	NPC57954
0.907	High Similarity	NPC213832
0.9048	High Similarity	NPC201655
0.8977	High Similarity	NPC287118
0.8977	High Similarity	NPC473690
0.8977	High Similarity	NPC471902
0.8953	High Similarity	NPC146937
0.8953	High Similarity	NPC471900
0.8941	High Similarity	NPC472505
0.8916	High Similarity	NPC170985
0.8889	High Similarity	NPC234564
0.8864	High Similarity	NPC471901
0.8864	High Similarity	NPC475416
0.8837	High Similarity	NPC264005
0.8837	High Similarity	NPC269360
0.8837	High Similarity	NPC33768
0.881	High Similarity	NPC471037
0.8804	High Similarity	NPC108371
0.8778	High Similarity	NPC210214
0.875	High Similarity	NPC169933
0.8721	High Similarity	NPC12774
0.8721	High Similarity	NPC2783
0.8721	High Similarity	NPC70661
0.869	High Similarity	NPC46881
0.8652	High Similarity	NPC154101
0.8642	High Similarity	NPC246445
0.8621	High Similarity	NPC96496
0.8605	High Similarity	NPC294438
0.8605	High Similarity	NPC264317
0.8588	High Similarity	NPC170862
0.8587	High Similarity	NPC253586
0.8571	High Similarity	NPC266431
0.8571	High Similarity	NPC263135
0.8571	High Similarity	NPC288906
0.8537	High Similarity	NPC66105
0.8526	High Similarity	NPC470310
0.8523	High Similarity	NPC255176
0.8523	High Similarity	NPC4309
0.8523	High Similarity	NPC474719
0.8523	High Similarity	NPC16377
0.8495	Intermediate Similarity	NPC16911
0.8495	Intermediate Similarity	NPC78427
0.8478	Intermediate Similarity	NPC13949
0.8478	Intermediate Similarity	NPC327788
0.8471	Intermediate Similarity	NPC474605
0.8471	Intermediate Similarity	NPC476292
0.8471	Intermediate Similarity	NPC110780
0.8471	Intermediate Similarity	NPC477935
0.8462	Intermediate Similarity	NPC47853
0.8444	Intermediate Similarity	NPC250753
0.8427	Intermediate Similarity	NPC220498
0.8427	Intermediate Similarity	NPC474570
0.8427	Intermediate Similarity	NPC54689
0.8427	Intermediate Similarity	NPC475921
0.8427	Intermediate Similarity	NPC476733
0.8427	Intermediate Similarity	NPC215029
0.8427	Intermediate Similarity	NPC474704
0.8421	Intermediate Similarity	NPC193934
0.8421	Intermediate Similarity	NPC271980
0.8415	Intermediate Similarity	NPC477933
0.8415	Intermediate Similarity	NPC477932
0.8404	Intermediate Similarity	NPC37047
0.8404	Intermediate Similarity	NPC287676
0.8404	Intermediate Similarity	NPC41971
0.8404	Intermediate Similarity	NPC94906
0.8404	Intermediate Similarity	NPC180733
0.8395	Intermediate Similarity	NPC477930
0.837	Intermediate Similarity	NPC263347
0.837	Intermediate Similarity	NPC469599
0.8352	Intermediate Similarity	NPC470375
0.8352	Intermediate Similarity	NPC294263
0.8352	Intermediate Similarity	NPC470376
0.8351	Intermediate Similarity	NPC265127
0.8333	Intermediate Similarity	NPC192744
0.8333	Intermediate Similarity	NPC201459
0.8316	Intermediate Similarity	NPC75941
0.8316	Intermediate Similarity	NPC289148
0.8316	Intermediate Similarity	NPC163963
0.8316	Intermediate Similarity	NPC52899
0.8315	Intermediate Similarity	NPC56413
0.8315	Intermediate Similarity	NPC183546
0.8315	Intermediate Similarity	NPC294480
0.8315	Intermediate Similarity	NPC328313
0.8313	Intermediate Similarity	NPC477918
0.8313	Intermediate Similarity	NPC68828
0.8313	Intermediate Similarity	NPC469867
0.8298	Intermediate Similarity	NPC472028
0.8295	Intermediate Similarity	NPC212843
0.8295	Intermediate Similarity	NPC155011
0.8295	Intermediate Similarity	NPC475007
0.8293	Intermediate Similarity	NPC477934
0.828	Intermediate Similarity	NPC329910
0.828	Intermediate Similarity	NPC120708
0.8276	Intermediate Similarity	NPC82902
0.8272	Intermediate Similarity	NPC279241
0.8272	Intermediate Similarity	NPC161187
0.8272	Intermediate Similarity	NPC330659
0.8272	Intermediate Similarity	NPC244708
0.8261	Intermediate Similarity	NPC470385
0.8261	Intermediate Similarity	NPC470386
0.8261	Intermediate Similarity	NPC277399
0.8256	Intermediate Similarity	NPC477858
0.8256	Intermediate Similarity	NPC477936
0.8256	Intermediate Similarity	NPC145143
0.8242	Intermediate Similarity	NPC160506
0.8242	Intermediate Similarity	NPC198242
0.8242	Intermediate Similarity	NPC211403
0.8242	Intermediate Similarity	NPC23434
0.8235	Intermediate Similarity	NPC476265
0.8235	Intermediate Similarity	NPC274522
0.8229	Intermediate Similarity	NPC214946
0.8229	Intermediate Similarity	NPC286519
0.8229	Intermediate Similarity	NPC148628
0.8229	Intermediate Similarity	NPC246736
0.8229	Intermediate Similarity	NPC88203
0.8229	Intermediate Similarity	NPC304832
0.8229	Intermediate Similarity	NPC124544
0.8229	Intermediate Similarity	NPC76866
0.8222	Intermediate Similarity	NPC247312
0.8222	Intermediate Similarity	NPC271974
0.8214	Intermediate Similarity	NPC476732
0.8214	Intermediate Similarity	NPC199965
0.8214	Intermediate Similarity	NPC63020
0.8202	Intermediate Similarity	NPC474684
0.8202	Intermediate Similarity	NPC57469
0.8202	Intermediate Similarity	NPC317590
0.8202	Intermediate Similarity	NPC142361
0.8202	Intermediate Similarity	NPC165895
0.8202	Intermediate Similarity	NPC312215
0.8191	Intermediate Similarity	NPC107243
0.8191	Intermediate Similarity	NPC57416
0.8191	Intermediate Similarity	NPC475894
0.8191	Intermediate Similarity	NPC156546
0.8182	Intermediate Similarity	NPC98270
0.8182	Intermediate Similarity	NPC474218
0.8182	Intermediate Similarity	NPC102292
0.8172	Intermediate Similarity	NPC470229
0.8172	Intermediate Similarity	NPC184848
0.8172	Intermediate Similarity	NPC470232
0.8172	Intermediate Similarity	NPC279974
0.8172	Intermediate Similarity	NPC69548
0.8163	Intermediate Similarity	NPC37600
0.8163	Intermediate Similarity	NPC295366
0.8161	Intermediate Similarity	NPC472743
0.8161	Intermediate Similarity	NPC475726
0.8161	Intermediate Similarity	NPC291320
0.8161	Intermediate Similarity	NPC471036
0.8161	Intermediate Similarity	NPC472498
0.8152	Intermediate Similarity	NPC244356
0.8152	Intermediate Similarity	NPC66429
0.8152	Intermediate Similarity	NPC291373
0.8152	Intermediate Similarity	NPC243866
0.8152	Intermediate Similarity	NPC224060
0.8152	Intermediate Similarity	NPC152897
0.8152	Intermediate Similarity	NPC206810
0.8144	Intermediate Similarity	NPC87927
0.8144	Intermediate Similarity	NPC469985
0.814	Intermediate Similarity	NPC474484
0.814	Intermediate Similarity	NPC103754
0.814	Intermediate Similarity	NPC232625
0.8132	Intermediate Similarity	NPC261994
0.8132	Intermediate Similarity	NPC471896
0.8132	Intermediate Similarity	NPC149761
0.8132	Intermediate Similarity	NPC171441
0.8132	Intermediate Similarity	NPC180849
0.8132	Intermediate Similarity	NPC470378
0.8125	Intermediate Similarity	NPC71706
0.8125	Intermediate Similarity	NPC46848
0.8125	Intermediate Similarity	NPC39683
0.8125	Intermediate Similarity	NPC121218
0.8125	Intermediate Similarity	NPC253886
0.8118	Intermediate Similarity	NPC471475
0.8111	Intermediate Similarity	NPC48824
0.8111	Intermediate Similarity	NPC160304
0.8111	Intermediate Similarity	NPC229407
0.8111	Intermediate Similarity	NPC254572
0.8111	Intermediate Similarity	NPC250687
0.8111	Intermediate Similarity	NPC242864
0.8105	Intermediate Similarity	NPC474793
0.8105	Intermediate Similarity	NPC119036
0.8105	Intermediate Similarity	NPC471038
0.8095	Intermediate Similarity	NPC471035
0.8095	Intermediate Similarity	NPC477919
0.8095	Intermediate Similarity	NPC474433
0.8095	Intermediate Similarity	NPC238227
0.8095	Intermediate Similarity	NPC106078
0.8095	Intermediate Similarity	NPC212661
0.8095	Intermediate Similarity	NPC180199
0.809	Intermediate Similarity	NPC55309
0.809	Intermediate Similarity	NPC28252
0.809	Intermediate Similarity	NPC469994
0.8085	Intermediate Similarity	NPC470387

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 NPC134197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1950
0.2-0.3	4098
0.3-0.4	1981
0.4-0.5	469
0.5-0.6	170
0.6-0.7	189
0.7-0.8	124
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD7520	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD4788	Approved
0.8242	Intermediate Similarity	NPD8034	Phase 2
0.8242	Intermediate Similarity	NPD8035	Phase 2
0.8191	Intermediate Similarity	NPD6083	Phase 2
0.8191	Intermediate Similarity	NPD6084	Phase 2
0.7976	Intermediate Similarity	NPD6117	Approved
0.7957	Intermediate Similarity	NPD6399	Phase 3
0.7952	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7146	Approved
0.7889	Intermediate Similarity	NPD5330	Approved
0.7889	Intermediate Similarity	NPD6409	Approved
0.7889	Intermediate Similarity	NPD7521	Approved
0.7889	Intermediate Similarity	NPD7334	Approved
0.7889	Intermediate Similarity	NPD6684	Approved
0.7882	Intermediate Similarity	NPD6116	Phase 1
0.7865	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD3666	Approved
0.7865	Intermediate Similarity	NPD4786	Approved
0.7865	Intermediate Similarity	NPD3665	Phase 1
0.7826	Intermediate Similarity	NPD4753	Phase 2
0.7805	Intermediate Similarity	NPD4245	Approved
0.7805	Intermediate Similarity	NPD4244	Approved
0.78	Intermediate Similarity	NPD5739	Approved
0.78	Intermediate Similarity	NPD7128	Approved
0.78	Intermediate Similarity	NPD6675	Approved
0.78	Intermediate Similarity	NPD6402	Approved
0.7791	Intermediate Similarity	NPD6118	Approved
0.7791	Intermediate Similarity	NPD6115	Approved
0.7791	Intermediate Similarity	NPD6697	Approved
0.7791	Intermediate Similarity	NPD6114	Approved
0.7789	Intermediate Similarity	NPD5695	Phase 3
0.7732	Intermediate Similarity	NPD5696	Approved
0.7717	Intermediate Similarity	NPD6903	Approved
0.7711	Intermediate Similarity	NPD5777	Approved
0.7683	Intermediate Similarity	NPD3698	Phase 2
0.7647	Intermediate Similarity	NPD3702	Approved
0.7647	Intermediate Similarity	NPD6899	Approved
0.7647	Intermediate Similarity	NPD6881	Approved
0.7647	Intermediate Similarity	NPD7320	Approved
0.764	Intermediate Similarity	NPD3667	Approved
0.7573	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD6372	Approved
0.7551	Intermediate Similarity	NPD7638	Approved
0.7549	Intermediate Similarity	NPD5701	Approved
0.7549	Intermediate Similarity	NPD5697	Approved
0.7527	Intermediate Similarity	NPD6672	Approved
0.7527	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6081	Approved
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.7475	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7474	Intermediate Similarity	NPD7515	Phase 2
0.7449	Intermediate Similarity	NPD4755	Approved
0.7447	Intermediate Similarity	NPD6673	Approved
0.7447	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD6080	Approved
0.7447	Intermediate Similarity	NPD6904	Approved
0.7444	Intermediate Similarity	NPD4221	Approved
0.7444	Intermediate Similarity	NPD4223	Phase 3
0.7429	Intermediate Similarity	NPD6869	Approved
0.7429	Intermediate Similarity	NPD6650	Approved
0.7429	Intermediate Similarity	NPD8130	Phase 1
0.7429	Intermediate Similarity	NPD6649	Approved
0.7429	Intermediate Similarity	NPD6617	Approved
0.7429	Intermediate Similarity	NPD6847	Approved
0.7423	Intermediate Similarity	NPD5210	Approved
0.7423	Intermediate Similarity	NPD4629	Approved
0.7404	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD6013	Approved
0.7404	Intermediate Similarity	NPD6014	Approved
0.7396	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD5329	Approved
0.7381	Intermediate Similarity	NPD4789	Approved
0.7358	Intermediate Similarity	NPD6882	Approved
0.7358	Intermediate Similarity	NPD8297	Approved
0.7333	Intermediate Similarity	NPD5369	Approved
0.732	Intermediate Similarity	NPD7748	Approved
0.7317	Intermediate Similarity	NPD4224	Phase 2
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.7308	Intermediate Similarity	NPD6011	Approved
0.73	Intermediate Similarity	NPD5286	Approved
0.73	Intermediate Similarity	NPD4700	Approved
0.73	Intermediate Similarity	NPD5285	Approved
0.73	Intermediate Similarity	NPD4696	Approved
0.7292	Intermediate Similarity	NPD5281	Approved
0.7292	Intermediate Similarity	NPD6079	Approved
0.7292	Intermediate Similarity	NPD5284	Approved
0.7292	Intermediate Similarity	NPD6411	Approved
0.7292	Intermediate Similarity	NPD7637	Suspended
0.7283	Intermediate Similarity	NPD4197	Approved
0.7264	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7525	Registered
0.7212	Intermediate Similarity	NPD6412	Phase 2
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5362	Discontinued
0.7159	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5208	Approved
0.7157	Intermediate Similarity	NPD5225	Approved
0.7157	Intermediate Similarity	NPD5224	Approved
0.7157	Intermediate Similarity	NPD5211	Phase 2
0.7157	Intermediate Similarity	NPD4633	Approved
0.7157	Intermediate Similarity	NPD5226	Approved
0.713	Intermediate Similarity	NPD8133	Approved
0.7128	Intermediate Similarity	NPD4138	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7128	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5205	Approved
0.7128	Intermediate Similarity	NPD4689	Approved
0.7128	Intermediate Similarity	NPD4690	Approved
0.7128	Intermediate Similarity	NPD4688	Approved
0.7128	Intermediate Similarity	NPD4693	Phase 3
0.7113	Intermediate Similarity	NPD5693	Phase 1
0.7113	Intermediate Similarity	NPD6050	Approved
0.71	Intermediate Similarity	NPD7902	Approved
0.7097	Intermediate Similarity	NPD3668	Phase 3
0.7091	Intermediate Similarity	NPD7115	Discovery
0.7087	Intermediate Similarity	NPD5175	Approved
0.7087	Intermediate Similarity	NPD5174	Approved
0.7083	Intermediate Similarity	NPD6051	Approved
0.7083	Intermediate Similarity	NPD6101	Approved
0.7083	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6435	Approved
0.7065	Intermediate Similarity	NPD4270	Approved
0.7065	Intermediate Similarity	NPD4269	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7054	Intermediate Similarity	NPD6319	Approved
0.7045	Intermediate Similarity	NPD7339	Approved
0.7045	Intermediate Similarity	NPD6942	Approved
0.7033	Intermediate Similarity	NPD5368	Approved
0.7019	Intermediate Similarity	NPD5141	Approved
0.701	Intermediate Similarity	NPD5692	Phase 3
0.701	Intermediate Similarity	NPD5785	Approved
0.7009	Intermediate Similarity	NPD4634	Approved
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD4697	Phase 3
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7632	Discontinued
0.6972	Remote Similarity	NPD4632	Approved
0.6964	Remote Similarity	NPD7101	Approved
0.6964	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD4139	Approved
0.6957	Remote Similarity	NPD7492	Approved
0.6957	Remote Similarity	NPD4692	Approved
0.6952	Remote Similarity	NPD4767	Approved
0.6952	Remote Similarity	NPD4768	Approved
0.6947	Remote Similarity	NPD5280	Approved
0.6947	Remote Similarity	NPD4694	Approved
0.6947	Remote Similarity	NPD5690	Phase 2
0.6947	Remote Similarity	NPD5786	Approved
0.6941	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5360	Phase 3
0.6939	Remote Similarity	NPD5694	Approved
0.6931	Remote Similarity	NPD5173	Approved
0.6923	Remote Similarity	NPD7736	Approved
0.6923	Remote Similarity	NPD4754	Approved
0.6903	Remote Similarity	NPD6054	Approved
0.6903	Remote Similarity	NPD6059	Approved
0.6897	Remote Similarity	NPD4243	Approved
0.6897	Remote Similarity	NPD6616	Approved
0.6875	Remote Similarity	NPD6335	Approved
0.6864	Remote Similarity	NPD7319	Approved
0.6854	Remote Similarity	NPD3703	Phase 2
0.6848	Remote Similarity	NPD4252	Approved
0.6842	Remote Similarity	NPD6909	Approved
0.6842	Remote Similarity	NPD6908	Approved
0.6842	Remote Similarity	NPD5363	Approved
0.6838	Remote Similarity	NPD7078	Approved
0.6838	Remote Similarity	NPD8293	Discontinued
0.6837	Remote Similarity	NPD5207	Approved
0.6822	Remote Similarity	NPD5128	Approved
0.6822	Remote Similarity	NPD4729	Approved
0.6822	Remote Similarity	NPD4730	Approved
0.6813	Remote Similarity	NPD3617	Approved
0.68	Remote Similarity	NPD6001	Approved
0.68	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD6008	Approved
0.679	Remote Similarity	NPD3198	Approved
0.6786	Remote Similarity	NPD6009	Approved
0.6786	Remote Similarity	NPD6317	Approved
0.6783	Remote Similarity	NPD6370	Approved
0.6752	Remote Similarity	NPD7507	Approved
0.6742	Remote Similarity	NPD4784	Approved
0.6742	Remote Similarity	NPD4785	Approved
0.6742	Remote Similarity	NPD6926	Approved
0.6742	Remote Similarity	NPD6924	Approved
0.6739	Remote Similarity	NPD7645	Phase 2

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