NPASS Compound

Structure

CID301707 OpenBabel06191716112D 34 37 0 0 1 0 0 0 0 0999 V2000 4.6144 2.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1923 3.1922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2873 -2.8816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1389 -2.3901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4659 0.5090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8816 -1.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0009 2.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6428 0.9485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2441 1.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6439 -1.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1086 -0.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2872 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6428 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 -1.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7701 2.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6439 0.9485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6663 2.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 1.4230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1923 1.5500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8219 1.4231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4659 -1.4236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6439 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1087 -1.4235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2873 -1.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4659 -0.4745 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8220 -0.4745 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 0.8220 2.3711 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6663 0.7289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8219 2.3965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9517 -1.9101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 3.3192 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 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 25 1 0 0 0 0 19 30 1 1 0 0 0 20 31 1 1 0 0 0 21 25 1 0 0 0 0 21 32 1 1 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 28 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 1 0 0 0 25 29 1 6 0 0 0 27 5 1 1 0 0 0 28 29 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.39
Volume:	525.735
LogP:	4.416
LogD:	4.59
LogS:	-4.246
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.06
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.772
MDCK Permeability:	2.5522169380565174e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.586
30% Bioavailability (F30%):	0.17

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	82.77801513671875%
Volume Distribution (VD):	0.946
Pgp-substrate:	12.860000610351562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.194
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.431
CYP3A4-inhibitor:	0.243
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	4.646
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.498
Carcinogencity:	0.015
Eye Corrosion:	0.355
Eye Irritation:	0.155
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC301707

Natural Product ID:	NPC301707
*Common Name:**	(20S,24S)-Dammarane-25(26)-Ene-3Beta,12Beta,20,24-Tetrol
IUPAC Name:	(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S,5S)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
Synonyms:
Standard InCHIKey:	CZGYKNXFDCANHD-YKJFMZFHSA-N
Standard InCHI:	InChI=1S/C30H52O4/c1-18(2)20(31)10-16-30(8,34)19-9-14-29(7)25(19)21(32)17-23-27(5)13-12-24(33)26(3,4)22(27)11-15-28(23,29)6/h19-25,31-34H,1,9-17H2,2-8H3/t19-,20-,21+,22-,23+,24-,25-,27-,28+,29+,30-/m0/s1
SMILES:	C=C(C)[C@H](CC[C@@](C)([C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2313417
PubChem CID:	71718556
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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	50000.0	nM	PMID[534751]

☑ 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 NPC301707 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	168
0.1-0.2	1964
0.2-0.3	8343
0.3-0.4	15461
0.4-0.5	6148
0.5-0.6	4991
0.6-0.7	4036
0.7-0.8	1265
0.8-0.85	219
0.85-0.9	51
0.9-0.95	47
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC185536
0.9583	High Similarity	NPC3403
0.9459	High Similarity	NPC472342
0.9324	High Similarity	NPC119355
0.9324	High Similarity	NPC257191
0.9324	High Similarity	NPC331618
0.9324	High Similarity	NPC248830
0.9324	High Similarity	NPC138502
0.9324	High Similarity	NPC212241
0.9211	High Similarity	NPC322313
0.9211	High Similarity	NPC236237
0.9211	High Similarity	NPC102253
0.92	High Similarity	NPC472501
0.9189	High Similarity	NPC38141
0.9189	High Similarity	NPC91573
0.9189	High Similarity	NPC14112
0.9189	High Similarity	NPC86305
0.9178	High Similarity	NPC476736
0.9167	High Similarity	NPC111234
0.9091	High Similarity	NPC157655
0.9079	High Similarity	NPC273410
0.9079	High Similarity	NPC80530
0.9079	High Similarity	NPC24504
0.9067	High Similarity	NPC307336
0.9067	High Similarity	NPC260301
0.9054	High Similarity	NPC70982
0.9054	High Similarity	NPC240235
0.9054	High Similarity	NPC230704
0.9054	High Similarity	NPC231256
0.9054	High Similarity	NPC104387
0.9054	High Similarity	NPC178383
0.9054	High Similarity	NPC212879
0.9028	High Similarity	NPC45296
0.8974	High Similarity	NPC296701
0.8974	High Similarity	NPC218616
0.8961	High Similarity	NPC71535
0.8961	High Similarity	NPC78545
0.8961	High Similarity	NPC47149
0.8947	High Similarity	NPC477819
0.8947	High Similarity	NPC42853
0.8947	High Similarity	NPC167037
0.8947	High Similarity	NPC285761
0.8947	High Similarity	NPC475
0.8947	High Similarity	NPC472502
0.8947	High Similarity	NPC477817
0.8947	High Similarity	NPC472499
0.8947	High Similarity	NPC6978
0.8947	High Similarity	NPC138621
0.8947	High Similarity	NPC31828
0.8947	High Similarity	NPC472500
0.8947	High Similarity	NPC244385
0.8933	High Similarity	NPC93662
0.8933	High Similarity	NPC278091
0.8933	High Similarity	NPC78067
0.8919	High Similarity	NPC145552
0.8919	High Similarity	NPC5046
0.8919	High Similarity	NPC196358
0.8919	High Similarity	NPC192638
0.8919	High Similarity	NPC49168
0.8919	High Similarity	NPC254509
0.8919	High Similarity	NPC62657
0.8919	High Similarity	NPC472503
0.8919	High Similarity	NPC308440
0.8919	High Similarity	NPC25511
0.8861	High Similarity	NPC216420
0.8861	High Similarity	NPC211135
0.8861	High Similarity	NPC232023
0.8861	High Similarity	NPC207013
0.8861	High Similarity	NPC85095
0.8831	High Similarity	NPC476316
0.8831	High Similarity	NPC49599
0.8831	High Similarity	NPC5604
0.8831	High Similarity	NPC49627
0.8816	High Similarity	NPC202540
0.88	High Similarity	NPC200243
0.8784	High Similarity	NPC472506
0.8784	High Similarity	NPC195489
0.875	High Similarity	NPC256567
0.8718	High Similarity	NPC13554
0.8718	High Similarity	NPC475679
0.8701	High Similarity	NPC102708
0.8684	High Similarity	NPC237460
0.8649	High Similarity	NPC164045
0.8625	High Similarity	NPC82623
0.8625	High Similarity	NPC470929
0.8625	High Similarity	NPC110778
0.859	High Similarity	NPC116119
0.859	High Similarity	NPC209430
0.859	High Similarity	NPC475727
0.859	High Similarity	NPC472742
0.859	High Similarity	NPC80297
0.859	High Similarity	NPC30986
0.8571	High Similarity	NPC470758
0.8571	High Similarity	NPC470711
0.8554	High Similarity	NPC67872
0.8553	High Similarity	NPC144075
0.8553	High Similarity	NPC103822
0.8537	High Similarity	NPC261266
0.8537	High Similarity	NPC139724
0.8537	High Similarity	NPC121981
0.8537	High Similarity	NPC201273
0.8537	High Similarity	NPC6391
0.8537	High Similarity	NPC168231
0.8519	High Similarity	NPC86238
0.8519	High Similarity	NPC255882
0.8519	High Similarity	NPC205845
0.85	High Similarity	NPC87489
0.85	High Similarity	NPC49964
0.85	High Similarity	NPC101462
0.85	High Similarity	NPC145143
0.85	High Similarity	NPC30166
0.85	High Similarity	NPC477599
0.8481	Intermediate Similarity	NPC164840
0.8481	Intermediate Similarity	NPC206735
0.8481	Intermediate Similarity	NPC241290
0.8481	Intermediate Similarity	NPC209944
0.8462	Intermediate Similarity	NPC474216
0.8462	Intermediate Similarity	NPC65897
0.8462	Intermediate Similarity	NPC302041
0.8462	Intermediate Similarity	NPC85346
0.8442	Intermediate Similarity	NPC73875
0.8442	Intermediate Similarity	NPC189883
0.8442	Intermediate Similarity	NPC470749
0.8434	Intermediate Similarity	NPC470620
0.8421	Intermediate Similarity	NPC469533
0.8421	Intermediate Similarity	NPC469534
0.8421	Intermediate Similarity	NPC469593
0.8415	Intermediate Similarity	NPC318390
0.8415	Intermediate Similarity	NPC292553
0.8395	Intermediate Similarity	NPC477818
0.8395	Intermediate Similarity	NPC141941
0.8395	Intermediate Similarity	NPC474634
0.8395	Intermediate Similarity	NPC193870
0.8395	Intermediate Similarity	NPC134481
0.8395	Intermediate Similarity	NPC470558
0.8378	Intermediate Similarity	NPC66407
0.8378	Intermediate Similarity	NPC9942
0.8378	Intermediate Similarity	NPC210323
0.8375	Intermediate Similarity	NPC264245
0.8356	Intermediate Similarity	NPC139207
0.8356	Intermediate Similarity	NPC185874
0.8354	Intermediate Similarity	NPC28862
0.8354	Intermediate Similarity	NPC109546
0.8354	Intermediate Similarity	NPC47982
0.8354	Intermediate Similarity	NPC143182
0.8354	Intermediate Similarity	NPC81306
0.8354	Intermediate Similarity	NPC1319
0.8354	Intermediate Similarity	NPC84694
0.8333	Intermediate Similarity	NPC133588
0.8333	Intermediate Similarity	NPC27243
0.8333	Intermediate Similarity	NPC160304
0.8333	Intermediate Similarity	NPC318495
0.8333	Intermediate Similarity	NPC16377
0.8333	Intermediate Similarity	NPC258595
0.8333	Intermediate Similarity	NPC155986
0.8333	Intermediate Similarity	NPC476737
0.8333	Intermediate Similarity	NPC198968
0.8333	Intermediate Similarity	NPC474668
0.8333	Intermediate Similarity	NPC214570
0.8313	Intermediate Similarity	NPC6605
0.8313	Intermediate Similarity	NPC24277
0.8313	Intermediate Similarity	NPC472738
0.8313	Intermediate Similarity	NPC299068
0.8312	Intermediate Similarity	NPC257347
0.8312	Intermediate Similarity	NPC118508
0.8312	Intermediate Similarity	NPC141071
0.8312	Intermediate Similarity	NPC121744
0.8312	Intermediate Similarity	NPC322353
0.8312	Intermediate Similarity	NPC471723
0.8293	Intermediate Similarity	NPC474047
0.8293	Intermediate Similarity	NPC470077
0.8293	Intermediate Similarity	NPC475798
0.8293	Intermediate Similarity	NPC478102
0.8293	Intermediate Similarity	NPC185568
0.8293	Intermediate Similarity	NPC231310
0.8293	Intermediate Similarity	NPC124172
0.8293	Intermediate Similarity	NPC127606
0.8289	Intermediate Similarity	NPC211009
0.8272	Intermediate Similarity	NPC202389
0.8272	Intermediate Similarity	NPC470049
0.8256	Intermediate Similarity	NPC41554
0.8256	Intermediate Similarity	NPC97404
0.825	Intermediate Similarity	NPC236112
0.825	Intermediate Similarity	NPC234193
0.8243	Intermediate Similarity	NPC245795
0.8243	Intermediate Similarity	NPC472741
0.8243	Intermediate Similarity	NPC276616
0.8243	Intermediate Similarity	NPC2648
0.8235	Intermediate Similarity	NPC470361
0.8228	Intermediate Similarity	NPC312328
0.8228	Intermediate Similarity	NPC473943
0.8228	Intermediate Similarity	NPC275910
0.8228	Intermediate Similarity	NPC11908
0.8214	Intermediate Similarity	NPC4643
0.8214	Intermediate Similarity	NPC477600
0.8214	Intermediate Similarity	NPC149224
0.8205	Intermediate Similarity	NPC202642
0.8205	Intermediate Similarity	NPC244488
0.8205	Intermediate Similarity	NPC46160
0.8205	Intermediate Similarity	NPC107059

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 NPC301707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	2276
0.2-0.3	4397
0.3-0.4	1645
0.4-0.5	275
0.5-0.6	168
0.6-0.7	172
0.7-0.8	66
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD7525	Registered
0.8133	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7339	Approved
0.8077	Intermediate Similarity	NPD6942	Approved
0.7976	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6926	Approved
0.7722	Intermediate Similarity	NPD6924	Approved
0.7683	Intermediate Similarity	NPD7645	Phase 2
0.7647	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8034	Phase 2
0.764	Intermediate Similarity	NPD8035	Phase 2
0.759	Intermediate Similarity	NPD6931	Approved
0.759	Intermediate Similarity	NPD6930	Phase 2
0.7586	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4787	Phase 1
0.7531	Intermediate Similarity	NPD6933	Approved
0.7529	Intermediate Similarity	NPD4788	Approved
0.7529	Intermediate Similarity	NPD6695	Phase 3
0.747	Intermediate Similarity	NPD6929	Approved
0.7468	Intermediate Similarity	NPD4243	Approved
0.7442	Intermediate Similarity	NPD4786	Approved
0.7439	Intermediate Similarity	NPD6116	Phase 1
0.7416	Intermediate Similarity	NPD5328	Approved
0.7381	Intermediate Similarity	NPD4748	Discontinued
0.7381	Intermediate Similarity	NPD7509	Discontinued
0.7363	Intermediate Similarity	NPD4202	Approved
0.7317	Intermediate Similarity	NPD6117	Approved
0.7292	Intermediate Similarity	NPD5211	Phase 2
0.7284	Intermediate Similarity	NPD4784	Approved
0.7284	Intermediate Similarity	NPD4785	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7263	Intermediate Similarity	NPD7640	Approved
0.7263	Intermediate Similarity	NPD7639	Approved
0.7253	Intermediate Similarity	NPD6079	Approved
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7150	Approved
0.725	Intermediate Similarity	NPD7151	Approved
0.725	Intermediate Similarity	NPD7152	Approved
0.7234	Intermediate Similarity	NPD4755	Approved
0.7229	Intermediate Similarity	NPD5776	Phase 2
0.7229	Intermediate Similarity	NPD6925	Approved
0.7215	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD6923	Approved
0.7209	Intermediate Similarity	NPD3667	Approved
0.7191	Intermediate Similarity	NPD7750	Discontinued
0.7191	Intermediate Similarity	NPD7524	Approved
0.7176	Intermediate Similarity	NPD7514	Phase 3
0.7159	Intermediate Similarity	NPD6893	Approved
0.7158	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD7145	Approved
0.7143	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD6697	Approved
0.7125	Intermediate Similarity	NPD7144	Approved
0.7125	Intermediate Similarity	NPD7143	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7073	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6932	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6399	Phase 3
0.6988	Remote Similarity	NPD5275	Approved
0.6988	Remote Similarity	NPD4190	Phase 3
0.6977	Remote Similarity	NPD7332	Phase 2
0.6947	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5221	Approved
0.6947	Remote Similarity	NPD5222	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6897	Remote Similarity	NPD6902	Approved
0.6897	Remote Similarity	NPD6898	Phase 1
0.6882	Remote Similarity	NPD7515	Phase 2
0.6882	Remote Similarity	NPD7087	Discontinued
0.6875	Remote Similarity	NPD5360	Phase 3
0.6875	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5173	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.686	Remote Similarity	NPD6683	Phase 2
0.686	Remote Similarity	NPD4195	Approved
0.6854	Remote Similarity	NPD3666	Approved
0.6854	Remote Similarity	NPD3665	Phase 1
0.6854	Remote Similarity	NPD3133	Approved
0.6848	Remote Similarity	NPD4753	Phase 2
0.6786	Remote Similarity	NPD3703	Phase 2
0.6786	Remote Similarity	NPD8264	Approved
0.6782	Remote Similarity	NPD6928	Phase 2
0.6768	Remote Similarity	NPD7632	Discontinued
0.6765	Remote Similarity	NPD6881	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6733	Remote Similarity	NPD4768	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6707	Remote Similarity	NPD4244	Approved
0.6707	Remote Similarity	NPD4245	Approved
0.6707	Remote Similarity	NPD4789	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6629	Remote Similarity	NPD4223	Phase 3
0.6629	Remote Similarity	NPD4221	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6593	Remote Similarity	NPD5329	Approved
0.6585	Remote Similarity	NPD3698	Phase 2
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6617	Approved
0.6562	Remote Similarity	NPD7748	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6538	Remote Similarity	NPD368	Approved
0.6531	Remote Similarity	NPD7902	Approved
0.6531	Remote Similarity	NPD6083	Phase 2
0.6531	Remote Similarity	NPD6084	Phase 2
0.6522	Remote Similarity	NPD5279	Phase 3
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7328	Approved
0.6514	Remote Similarity	NPD7327	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6509	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4629	Approved
0.6495	Remote Similarity	NPD5210	Approved
0.6484	Remote Similarity	NPD4197	Approved
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5249	Phase 3
0.6476	Remote Similarity	NPD5135	Approved
0.6465	Remote Similarity	NPD5290	Discontinued
0.6455	Remote Similarity	NPD7516	Approved
0.6449	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD4758	Discontinued
0.6422	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD5216	Approved
0.6415	Remote Similarity	NPD5215	Approved
0.6415	Remote Similarity	NPD5127	Approved
0.6415	Remote Similarity	NPD5217	Approved
0.6396	Remote Similarity	NPD8294	Approved
0.6396	Remote Similarity	NPD8377	Approved
0.6364	Remote Similarity	NPD5364	Discontinued
0.6364	Remote Similarity	NPD3671	Phase 1
0.6354	Remote Similarity	NPD7637	Suspended
0.6344	Remote Similarity	NPD4690	Approved
0.6344	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD5205	Approved
0.6344	Remote Similarity	NPD4693	Phase 3
0.6344	Remote Similarity	NPD4689	Approved
0.6344	Remote Similarity	NPD4138	Approved
0.6339	Remote Similarity	NPD8033	Approved
0.6339	Remote Similarity	NPD8378	Approved
0.6339	Remote Similarity	NPD8296	Approved
0.6339	Remote Similarity	NPD8380	Approved
0.6339	Remote Similarity	NPD8335	Approved
0.6339	Remote Similarity	NPD8379	Approved
0.6337	Remote Similarity	NPD4159	Approved
0.63	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD4632	Approved
0.6286	Remote Similarity	NPD5168	Approved
0.6265	Remote Similarity	NPD6705	Phase 1
0.625	Remote Similarity	NPD7136	Phase 2
0.625	Remote Similarity	NPD6700	Approved
0.625	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5167	Approved
0.6235	Remote Similarity	NPD6081	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