NPASS Compound

Structure

NPC76518 OpenBabel07101719252D 32 36 0 0 1 0 0 0 0 0999 V2000 -4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5446 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 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 -1.7321 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9266 2.8838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 20 3 1 1 0 0 0 20 21 1 0 0 0 0 21 27 1 6 0 0 0 22 31 2 0 0 0 0 23 26 1 0 0 0 0 23 29 1 6 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	6.669
LogD:	5.365
LogS:	-5.713
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	5.455
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.097
MDCK Permeability:	1.560004056955222e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.767
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	92.49247741699219%
Volume Distribution (VD):	1.021
Pgp-substrate:	1.8583381175994873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.318
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.312
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.372
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.676

ADMET: Excretion

Clearance (CL):	8.735
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.213
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.068
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.545
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.952
Carcinogencity:	0.107
Eye Corrosion:	0.661
Eye Irritation:	0.264
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC76518

Natural Product ID:	NPC76518
*Common Name:**	IUKHRGYJJZRAQW-XLWCLXEDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IUKHRGYJJZRAQW-XLWCLXEDSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19(2)22(31)9-8-20(3)21-12-14-28(7)24-11-10-23-26(4,5)25(32)13-15-29(23)18-30(24,29)17-16-27(21,28)6/h20-21,23-25,32H,1,8-18H2,2-7H3/t20-,21-,23+,24+,25+,27-,28+,29-,30+/m1/s1
SMILES:	CC(=C)C(=O)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376382
PubChem CID:	44423571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11858752]
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]

☑ 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
Others	6

Activity Type	# Activity
Cell Line	1
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[530968]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	1.5	%	PMID[530968]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	25.4	%	PMID[530968]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	73.1	%	PMID[530968]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	97.8	%	PMID[530968]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	9.3	nM	PMID[530968]
NPT2	Others	Unspecified		Activity	=	1.4	n.a.	PMID[530968]

☑ 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 NPC76518 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	188
0.1-0.2	1706
0.2-0.3	7322
0.3-0.4	15671
0.4-0.5	6080
0.5-0.6	5694
0.6-0.7	4220
0.7-0.8	1530
0.8-0.85	221
0.85-0.9	56
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC472743
0.9259	High Similarity	NPC291320
0.9259	High Similarity	NPC475726
0.9259	High Similarity	NPC471036
0.9167	High Similarity	NPC472739
0.9157	High Similarity	NPC98236
0.9157	High Similarity	NPC269396
0.9146	High Similarity	NPC475745
0.9146	High Similarity	NPC146683
0.9146	High Similarity	NPC474482
0.9136	High Similarity	NPC477858
0.9036	High Similarity	NPC471034
0.9036	High Similarity	NPC292553
0.9036	High Similarity	NPC190704
0.9024	High Similarity	NPC118800
0.8987	High Similarity	NPC106078
0.8966	High Similarity	NPC12722
0.8953	High Similarity	NPC126993
0.8941	High Similarity	NPC146937
0.8929	High Similarity	NPC472738
0.8916	High Similarity	NPC264665
0.8916	High Similarity	NPC474233
0.8916	High Similarity	NPC74595
0.8889	High Similarity	NPC164999
0.8851	High Similarity	NPC272746
0.8824	High Similarity	NPC259009
0.8824	High Similarity	NPC165895
0.8824	High Similarity	NPC57469
0.8824	High Similarity	NPC4643
0.8824	High Similarity	NPC153604
0.8824	High Similarity	NPC174619
0.881	High Similarity	NPC294438
0.881	High Similarity	NPC102292
0.881	High Similarity	NPC264317
0.8795	High Similarity	NPC175410
0.8765	High Similarity	NPC201459
0.8736	High Similarity	NPC85173
0.8734	High Similarity	NPC273366
0.8734	High Similarity	NPC70982
0.8734	High Similarity	NPC230704
0.8721	High Similarity	NPC193360
0.8721	High Similarity	NPC471724
0.8721	High Similarity	NPC474719
0.8706	High Similarity	NPC2783
0.8706	High Similarity	NPC70661
0.8706	High Similarity	NPC72133
0.8706	High Similarity	NPC12774
0.8675	High Similarity	NPC110780
0.8675	High Similarity	NPC145143
0.8621	High Similarity	NPC122116
0.8608	High Similarity	NPC254509
0.8608	High Similarity	NPC196358
0.8608	High Similarity	NPC49168
0.8608	High Similarity	NPC5046
0.8608	High Similarity	NPC145552
0.8605	High Similarity	NPC89747
0.8605	High Similarity	NPC264005
0.8605	High Similarity	NPC475740
0.8605	High Similarity	NPC269360
0.8605	High Similarity	NPC33768
0.8588	High Similarity	NPC22133
0.8588	High Similarity	NPC470574
0.8556	High Similarity	NPC266431
0.8554	High Similarity	NPC474484
0.8554	High Similarity	NPC103754
0.8539	High Similarity	NPC294263
0.8523	High Similarity	NPC46758
0.8523	High Similarity	NPC261994
0.8523	High Similarity	NPC470378
0.8523	High Similarity	NPC180849
0.8523	High Similarity	NPC191684
0.8523	High Similarity	NPC149761
0.8523	High Similarity	NPC80401
0.8519	High Similarity	NPC331618
0.8519	High Similarity	NPC475031
0.8519	High Similarity	NPC472746
0.8519	High Similarity	NPC149249
0.8519	High Similarity	NPC257191
0.8506	High Similarity	NPC143767
0.8506	High Similarity	NPC328539
0.8506	High Similarity	NPC131470
0.8506	High Similarity	NPC474677
0.8506	High Similarity	NPC16377
0.8506	High Similarity	NPC471722
0.8506	High Similarity	NPC471900
0.85	High Similarity	NPC200243
0.8495	Intermediate Similarity	NPC71706
0.8488	Intermediate Similarity	NPC145879
0.8488	Intermediate Similarity	NPC31564
0.8488	Intermediate Similarity	NPC474732
0.8488	Intermediate Similarity	NPC474778
0.8488	Intermediate Similarity	NPC474733
0.8481	Intermediate Similarity	NPC195489
0.8481	Intermediate Similarity	NPC232112
0.8471	Intermediate Similarity	NPC221758
0.8471	Intermediate Similarity	NPC214043
0.8471	Intermediate Similarity	NPC85774
0.8471	Intermediate Similarity	NPC59453
0.8444	Intermediate Similarity	NPC47853
0.8427	Intermediate Similarity	NPC211403
0.8427	Intermediate Similarity	NPC299185
0.8427	Intermediate Similarity	NPC476168
0.8427	Intermediate Similarity	NPC198242
0.8415	Intermediate Similarity	NPC472342
0.8409	Intermediate Similarity	NPC128496
0.8409	Intermediate Similarity	NPC213832
0.8409	Intermediate Similarity	NPC220498
0.8409	Intermediate Similarity	NPC57954
0.8409	Intermediate Similarity	NPC1015
0.8409	Intermediate Similarity	NPC31985
0.8409	Intermediate Similarity	NPC119416
0.8409	Intermediate Similarity	NPC275740
0.8409	Intermediate Similarity	NPC86319
0.8409	Intermediate Similarity	NPC473999
0.8409	Intermediate Similarity	NPC309603
0.8391	Intermediate Similarity	NPC93778
0.8391	Intermediate Similarity	NPC472495
0.8391	Intermediate Similarity	NPC141292
0.8391	Intermediate Similarity	NPC472497
0.8391	Intermediate Similarity	NPC58063
0.8391	Intermediate Similarity	NPC142361
0.8391	Intermediate Similarity	NPC474684
0.8354	Intermediate Similarity	NPC58057
0.8354	Intermediate Similarity	NPC151018
0.8354	Intermediate Similarity	NPC320549
0.8354	Intermediate Similarity	NPC111234
0.8354	Intermediate Similarity	NPC156277
0.8353	Intermediate Similarity	NPC471037
0.8353	Intermediate Similarity	NPC245866
0.8352	Intermediate Similarity	NPC263135
0.8352	Intermediate Similarity	NPC476174
0.8352	Intermediate Similarity	NPC98639
0.8352	Intermediate Similarity	NPC210214
0.8352	Intermediate Similarity	NPC288906
0.8333	Intermediate Similarity	NPC475255
0.8333	Intermediate Similarity	NPC244356
0.8333	Intermediate Similarity	NPC59350
0.8333	Intermediate Similarity	NPC224060
0.8333	Intermediate Similarity	NPC181594
0.8333	Intermediate Similarity	NPC144739
0.8333	Intermediate Similarity	NPC328264
0.8333	Intermediate Similarity	NPC59170
0.8316	Intermediate Similarity	NPC470310
0.8315	Intermediate Similarity	NPC183283
0.8315	Intermediate Similarity	NPC169933
0.8315	Intermediate Similarity	NPC48010
0.8313	Intermediate Similarity	NPC476812
0.8295	Intermediate Similarity	NPC4309
0.8295	Intermediate Similarity	NPC292491
0.8295	Intermediate Similarity	NPC310752
0.8293	Intermediate Similarity	NPC471035
0.8293	Intermediate Similarity	NPC212661
0.8276	Intermediate Similarity	NPC158393
0.8276	Intermediate Similarity	NPC51014
0.8276	Intermediate Similarity	NPC471737
0.8276	Intermediate Similarity	NPC28252
0.8276	Intermediate Similarity	NPC34190
0.8276	Intermediate Similarity	NPC94755
0.8276	Intermediate Similarity	NPC55309
0.8272	Intermediate Similarity	NPC97534
0.8272	Intermediate Similarity	NPC185536
0.8272	Intermediate Similarity	NPC104387
0.8272	Intermediate Similarity	NPC174964
0.8272	Intermediate Similarity	NPC240235
0.8272	Intermediate Similarity	NPC195155
0.8272	Intermediate Similarity	NPC212879
0.8272	Intermediate Similarity	NPC178383
0.8272	Intermediate Similarity	NPC3403
0.8272	Intermediate Similarity	NPC231256
0.8261	Intermediate Similarity	NPC200054
0.8261	Intermediate Similarity	NPC160056
0.8261	Intermediate Similarity	NPC329910
0.8261	Intermediate Similarity	NPC29410
0.8261	Intermediate Similarity	NPC234564
0.8256	Intermediate Similarity	NPC473246
0.8256	Intermediate Similarity	NPC82902
0.8256	Intermediate Similarity	NPC472265
0.8242	Intermediate Similarity	NPC196485
0.8242	Intermediate Similarity	NPC302008
0.8242	Intermediate Similarity	NPC215271
0.8242	Intermediate Similarity	NPC470385
0.8242	Intermediate Similarity	NPC153775
0.8242	Intermediate Similarity	NPC29247
0.8242	Intermediate Similarity	NPC470386
0.8242	Intermediate Similarity	NPC209662
0.8242	Intermediate Similarity	NPC289539
0.8242	Intermediate Similarity	NPC292374
0.8242	Intermediate Similarity	NPC245972
0.8242	Intermediate Similarity	NPC261333
0.8242	Intermediate Similarity	NPC64006
0.8242	Intermediate Similarity	NPC104371
0.8242	Intermediate Similarity	NPC191094
0.8242	Intermediate Similarity	NPC111524
0.8242	Intermediate Similarity	NPC101233
0.8242	Intermediate Similarity	NPC91772
0.8242	Intermediate Similarity	NPC129004
0.8242	Intermediate Similarity	NPC111015
0.8235	Intermediate Similarity	NPC46881
0.8235	Intermediate Similarity	NPC151519
0.8228	Intermediate Similarity	NPC45296

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 NPC76518 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2144
0.2-0.3	4376
0.3-0.4	1700
0.4-0.5	356
0.5-0.6	137
0.6-0.7	140
0.7-0.8	116
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD7520	Clinical (unspecified phase)
0.8795	High Similarity	NPD4788	Approved
0.8636	High Similarity	NPD6079	Approved
0.8621	High Similarity	NPD5328	Approved
0.8488	Intermediate Similarity	NPD3618	Phase 1
0.8471	Intermediate Similarity	NPD4786	Approved
0.8354	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3667	Approved
0.8132	Intermediate Similarity	NPD4202	Approved
0.8101	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5222	Approved
0.8065	Intermediate Similarity	NPD5221	Approved
0.8065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD3666	Approved
0.8046	Intermediate Similarity	NPD3133	Approved
0.8046	Intermediate Similarity	NPD3665	Phase 1
0.8022	Intermediate Similarity	NPD8035	Phase 2
0.8022	Intermediate Similarity	NPD8034	Phase 2
0.7979	Intermediate Similarity	NPD5173	Approved
0.7952	Intermediate Similarity	NPD6117	Approved
0.7927	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4697	Phase 3
0.7857	Intermediate Similarity	NPD6116	Phase 1
0.7831	Intermediate Similarity	NPD3703	Phase 2
0.7826	Intermediate Similarity	NPD7515	Phase 2
0.7812	Intermediate Similarity	NPD5285	Approved
0.7812	Intermediate Similarity	NPD5286	Approved
0.7812	Intermediate Similarity	NPD4696	Approved
0.7791	Intermediate Similarity	NPD7525	Registered
0.7789	Intermediate Similarity	NPD4755	Approved
0.7778	Intermediate Similarity	NPD4245	Approved
0.7778	Intermediate Similarity	NPD4244	Approved
0.7778	Intermediate Similarity	NPD4789	Approved
0.7765	Intermediate Similarity	NPD6118	Approved
0.7765	Intermediate Similarity	NPD6697	Approved
0.7765	Intermediate Similarity	NPD6114	Approved
0.7765	Intermediate Similarity	NPD6115	Approved
0.775	Intermediate Similarity	NPD5360	Phase 3
0.775	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD5223	Approved
0.7667	Intermediate Similarity	NPD5279	Phase 3
0.7654	Intermediate Similarity	NPD3698	Phase 2
0.7653	Intermediate Similarity	NPD5225	Approved
0.7653	Intermediate Similarity	NPD5226	Approved
0.7653	Intermediate Similarity	NPD5211	Phase 2
0.7653	Intermediate Similarity	NPD4633	Approved
0.7653	Intermediate Similarity	NPD5224	Approved
0.7629	Intermediate Similarity	NPD4700	Approved
0.7614	Intermediate Similarity	NPD4221	Approved
0.7614	Intermediate Similarity	NPD4223	Phase 3
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7595	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5175	Approved
0.7576	Intermediate Similarity	NPD5174	Approved
0.7556	Intermediate Similarity	NPD5329	Approved
0.7553	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD5141	Approved
0.7474	Intermediate Similarity	NPD7748	Approved
0.7473	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6899	Approved
0.7451	Intermediate Similarity	NPD6881	Approved
0.7444	Intermediate Similarity	NPD3668	Phase 3
0.7444	Intermediate Similarity	NPD4197	Approved
0.7426	Intermediate Similarity	NPD6675	Approved
0.7426	Intermediate Similarity	NPD7128	Approved
0.7426	Intermediate Similarity	NPD6402	Approved
0.7426	Intermediate Similarity	NPD5739	Approved
0.7412	Intermediate Similarity	NPD7339	Approved
0.7412	Intermediate Similarity	NPD6942	Approved
0.74	Intermediate Similarity	NPD4754	Approved
0.7396	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD4629	Approved
0.7356	Intermediate Similarity	NPD3617	Approved
0.7356	Intermediate Similarity	NPD3671	Phase 1
0.7353	Intermediate Similarity	NPD5697	Approved
0.7347	Intermediate Similarity	NPD7638	Approved
0.7312	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7102	Approved
0.7308	Intermediate Similarity	NPD7290	Approved
0.7308	Intermediate Similarity	NPD6883	Approved
0.7283	Intermediate Similarity	NPD7146	Approved
0.7283	Intermediate Similarity	NPD4689	Approved
0.7283	Intermediate Similarity	NPD4690	Approved
0.7283	Intermediate Similarity	NPD4138	Approved
0.7283	Intermediate Similarity	NPD7521	Approved
0.7283	Intermediate Similarity	NPD6409	Approved
0.7283	Intermediate Similarity	NPD4688	Approved
0.7283	Intermediate Similarity	NPD5330	Approved
0.7283	Intermediate Similarity	NPD4693	Phase 3
0.7283	Intermediate Similarity	NPD6684	Approved
0.7283	Intermediate Similarity	NPD5205	Approved
0.7283	Intermediate Similarity	NPD7334	Approved
0.7283	Intermediate Similarity	NPD5690	Phase 2
0.7282	Intermediate Similarity	NPD5128	Approved
0.7282	Intermediate Similarity	NPD7320	Approved
0.7282	Intermediate Similarity	NPD4730	Approved
0.7282	Intermediate Similarity	NPD5168	Approved
0.7282	Intermediate Similarity	NPD6011	Approved
0.7282	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7262	Intermediate Similarity	NPD4758	Discontinued
0.7255	Intermediate Similarity	NPD4767	Approved
0.7255	Intermediate Similarity	NPD4768	Approved
0.7245	Intermediate Similarity	NPD6084	Phase 2
0.7245	Intermediate Similarity	NPD7902	Approved
0.7245	Intermediate Similarity	NPD6083	Phase 2
0.7238	Intermediate Similarity	NPD6617	Approved
0.7238	Intermediate Similarity	NPD6869	Approved
0.7238	Intermediate Similarity	NPD6650	Approved
0.7238	Intermediate Similarity	NPD6847	Approved
0.7238	Intermediate Similarity	NPD6649	Approved
0.7238	Intermediate Similarity	NPD8130	Phase 1
0.7216	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD6012	Approved
0.7212	Intermediate Similarity	NPD6013	Approved
0.7212	Intermediate Similarity	NPD6014	Approved
0.7212	Intermediate Similarity	NPD6373	Approved
0.7184	Intermediate Similarity	NPD5701	Approved
0.717	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5250	Approved
0.7128	Intermediate Similarity	NPD5737	Approved
0.7128	Intermediate Similarity	NPD6672	Approved
0.7128	Intermediate Similarity	NPD6903	Approved
0.7126	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4694	Approved
0.7097	Intermediate Similarity	NPD5280	Approved
0.7079	Intermediate Similarity	NPD7645	Phase 2
0.7079	Intermediate Similarity	NPD4195	Approved
0.7075	Intermediate Similarity	NPD5215	Approved
0.7075	Intermediate Similarity	NPD5127	Approved
0.7075	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5217	Approved
0.7075	Intermediate Similarity	NPD5216	Approved
0.7073	Intermediate Similarity	NPD4224	Phase 2
0.7064	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD6081	Approved
0.7024	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4695	Discontinued
0.6972	Remote Similarity	NPD6868	Approved
0.6966	Remote Similarity	NPD5364	Discontinued
0.6944	Remote Similarity	NPD4632	Approved
0.6941	Remote Similarity	NPD4747	Approved
0.6941	Remote Similarity	NPD4691	Approved
0.6939	Remote Similarity	NPD6001	Approved
0.6939	Remote Similarity	NPD7900	Approved
0.6939	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD4692	Approved
0.6897	Remote Similarity	NPD6926	Approved
0.6897	Remote Similarity	NPD6924	Approved
0.6881	Remote Similarity	NPD5167	Approved
0.6869	Remote Similarity	NPD5695	Phase 3
0.686	Remote Similarity	NPD5777	Approved
0.6847	Remote Similarity	NPD6335	Approved
0.6842	Remote Similarity	NPD7604	Phase 2
0.6837	Remote Similarity	NPD5133	Approved
0.6832	Remote Similarity	NPD5696	Approved
0.6832	Remote Similarity	NPD5290	Discontinued
0.6824	Remote Similarity	NPD4137	Phase 3
0.6818	Remote Similarity	NPD6274	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6786	Remote Similarity	NPD7100	Approved
0.6786	Remote Similarity	NPD7101	Approved
0.6762	Remote Similarity	NPD6008	Approved
0.6757	Remote Similarity	NPD6009	Approved
0.6757	Remote Similarity	NPD6317	Approved
0.6744	Remote Similarity	NPD4787	Phase 1
0.6742	Remote Similarity	NPD6933	Approved
0.6737	Remote Similarity	NPD6098	Approved
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6735	Remote Similarity	NPD5281	Approved
0.6735	Remote Similarity	NPD5284	Approved
0.6726	Remote Similarity	NPD6054	Approved
0.6705	Remote Similarity	NPD4058	Approved
0.6705	Remote Similarity	NPD5733	Approved
0.6701	Remote Similarity	NPD6080	Approved
0.6701	Remote Similarity	NPD6904	Approved
0.6701	Remote Similarity	NPD6673	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD6313	Approved
0.6696	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD3573	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