NPASS Compound

Structure

NPC20388 OpenBabel07101718182D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.8234 -3.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 -2.1488 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 -3.8745 -1.1977 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 -1.2024 1.0827 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 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 -3.5144 -2.8920 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5873 -0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 -0.9898 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 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 -2.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8671 -3.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 -1.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 19 2 1 1 0 0 0 19 20 1 0 0 0 0 20 29 1 1 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 22 30 1 0 0 0 0 23 19 1 1 0 0 0 23 33 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 31 1 6 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	6.09
LogD:	4.765
LogS:	-6.487
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	4.946
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.007
MDCK Permeability:	2.348120506212581e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	92.7915267944336%
Volume Distribution (VD):	1.207
Pgp-substrate:	1.2763426303863525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.603
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.63
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	5.756
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.57
Carcinogencity:	0.017
Eye Corrosion:	0.029
Eye Irritation:	0.17
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC20388

Natural Product ID:	NPC20388
*Common Name:**	3-Epi-Astrahygrol
IUPAC Name:	(3S,6S)-6-[(1S)-1-[(3R,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-methyloxan-2-one
Synonyms:	3-Epi-Astrahygrol
Standard InCHIKey:	RAVLYMWHELNCTR-QWUYLKCSSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18-8-10-23(33-26(18)32)19(2)20-12-16-30(7)22-9-11-24-27(3,4)25(31)14-15-28(24,5)21(22)13-17-29(20,30)6/h18-20,23-25,31H,8-17H2,1-7H3/t18-,19-,20+,23-,24-,25+,28+,29+,30-/m0/s1
SMILES:	C[C@H]1CC[C@H](OC1=O)[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454686
PubChem CID:	44563601
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO22791	Astraeus pteridis	Species	Astraeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19067555]
NPO22791	Astraeus pteridis	Species	Astraeaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	58.0	ug.mL-1	PMID[472653]

☑ 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 NPC20388 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	193
0.1-0.2	1409
0.2-0.3	5612
0.3-0.4	14880
0.4-0.5	7090
0.5-0.6	5674
0.6-0.7	5107
0.7-0.8	2522
0.8-0.85	178
0.85-0.9	30
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.907	High Similarity	NPC55309
0.907	High Similarity	NPC28252
0.9059	High Similarity	NPC109512
0.8977	High Similarity	NPC474889
0.8966	High Similarity	NPC187376
0.8966	High Similarity	NPC159046
0.8966	High Similarity	NPC233836
0.8901	High Similarity	NPC470016
0.8901	High Similarity	NPC317586
0.8876	High Similarity	NPC111585
0.8876	High Similarity	NPC175628
0.8876	High Similarity	NPC148414
0.8864	High Similarity	NPC242864
0.8791	High Similarity	NPC471720
0.8791	High Similarity	NPC184870
0.8791	High Similarity	NPC166906
0.8778	High Similarity	NPC26888
0.8764	High Similarity	NPC84271
0.8764	High Similarity	NPC102414
0.8764	High Similarity	NPC77168
0.875	High Similarity	NPC142361
0.875	High Similarity	NPC474684
0.8696	High Similarity	NPC48330
0.8696	High Similarity	NPC255809
0.8696	High Similarity	NPC184848
0.8696	High Similarity	NPC69548
0.8681	High Similarity	NPC470224
0.8681	High Similarity	NPC470254
0.8667	High Similarity	NPC471896
0.8667	High Similarity	NPC469400
0.8652	High Similarity	NPC131470
0.8652	High Similarity	NPC143767
0.8621	High Similarity	NPC171789
0.8602	High Similarity	NPC7124
0.8602	High Similarity	NPC96859
0.8602	High Similarity	NPC328162
0.8602	High Similarity	NPC95565
0.8602	High Similarity	NPC305483
0.8602	High Similarity	NPC173272
0.8602	High Similarity	NPC120708
0.8587	High Similarity	NPC240617
0.8587	High Similarity	NPC303863
0.8571	High Similarity	NPC23434
0.8571	High Similarity	NPC107690
0.8571	High Similarity	NPC297265
0.8556	High Similarity	NPC475921
0.8556	High Similarity	NPC275740
0.8556	High Similarity	NPC86319
0.8556	High Similarity	NPC474704
0.8526	High Similarity	NPC88198
0.8511	High Similarity	NPC121339
0.8495	Intermediate Similarity	NPC473648
0.8478	Intermediate Similarity	NPC477855
0.8462	Intermediate Similarity	NPC44240
0.8462	Intermediate Similarity	NPC219495
0.8462	Intermediate Similarity	NPC183283
0.8462	Intermediate Similarity	NPC289213
0.8454	Intermediate Similarity	NPC70967
0.8454	Intermediate Similarity	NPC33973
0.8427	Intermediate Similarity	NPC72133
0.8427	Intermediate Similarity	NPC12774
0.8427	Intermediate Similarity	NPC155011
0.8427	Intermediate Similarity	NPC325594
0.8427	Intermediate Similarity	NPC94755
0.8421	Intermediate Similarity	NPC477813
0.8404	Intermediate Similarity	NPC328371
0.8404	Intermediate Similarity	NPC3772
0.8387	Intermediate Similarity	NPC469406
0.837	Intermediate Similarity	NPC63748
0.837	Intermediate Similarity	NPC189520
0.8367	Intermediate Similarity	NPC216245
0.8367	Intermediate Similarity	NPC470251
0.8367	Intermediate Similarity	NPC2436
0.8367	Intermediate Similarity	NPC135854
0.8351	Intermediate Similarity	NPC473788
0.8351	Intermediate Similarity	NPC475558
0.8333	Intermediate Similarity	NPC316964
0.8333	Intermediate Similarity	NPC307954
0.8333	Intermediate Similarity	NPC138756
0.8333	Intermediate Similarity	NPC33768
0.8333	Intermediate Similarity	NPC157787
0.8316	Intermediate Similarity	NPC106557
0.8316	Intermediate Similarity	NPC18319
0.8316	Intermediate Similarity	NPC43747
0.8315	Intermediate Similarity	NPC294438
0.8315	Intermediate Similarity	NPC264317
0.8298	Intermediate Similarity	NPC174948
0.8298	Intermediate Similarity	NPC469995
0.8298	Intermediate Similarity	NPC45324
0.8298	Intermediate Similarity	NPC162001
0.8298	Intermediate Similarity	NPC222845
0.8298	Intermediate Similarity	NPC469599
0.8298	Intermediate Similarity	NPC318282
0.8298	Intermediate Similarity	NPC279974
0.8298	Intermediate Similarity	NPC37646
0.8298	Intermediate Similarity	NPC173875
0.8283	Intermediate Similarity	NPC231530
0.8283	Intermediate Similarity	NPC278628
0.828	Intermediate Similarity	NPC107674
0.828	Intermediate Similarity	NPC49776
0.828	Intermediate Similarity	NPC470376
0.828	Intermediate Similarity	NPC63118
0.828	Intermediate Similarity	NPC206810
0.828	Intermediate Similarity	NPC69454
0.828	Intermediate Similarity	NPC27918
0.828	Intermediate Similarity	NPC170220
0.828	Intermediate Similarity	NPC474436
0.828	Intermediate Similarity	NPC470375
0.828	Intermediate Similarity	NPC141497
0.828	Intermediate Similarity	NPC25750
0.8261	Intermediate Similarity	NPC136801
0.8247	Intermediate Similarity	NPC474327
0.8247	Intermediate Similarity	NPC124211
0.8242	Intermediate Similarity	NPC328539
0.8242	Intermediate Similarity	NPC471724
0.8242	Intermediate Similarity	NPC471722
0.8242	Intermediate Similarity	NPC40552
0.8242	Intermediate Similarity	NPC4309
0.8242	Intermediate Similarity	NPC53911
0.8242	Intermediate Similarity	NPC246708
0.8229	Intermediate Similarity	NPC477854
0.8222	Intermediate Similarity	NPC474970
0.8222	Intermediate Similarity	NPC2783
0.8222	Intermediate Similarity	NPC73038
0.8222	Intermediate Similarity	NPC56588
0.8222	Intermediate Similarity	NPC72638
0.8211	Intermediate Similarity	NPC125622
0.8211	Intermediate Similarity	NPC42042
0.8211	Intermediate Similarity	NPC243525
0.8211	Intermediate Similarity	NPC471822
0.8211	Intermediate Similarity	NPC40765
0.8202	Intermediate Similarity	NPC165064
0.82	Intermediate Similarity	NPC473037
0.8191	Intermediate Similarity	NPC159410
0.8182	Intermediate Similarity	NPC96268
0.8182	Intermediate Similarity	NPC73882
0.8182	Intermediate Similarity	NPC471293
0.8182	Intermediate Similarity	NPC28656
0.8172	Intermediate Similarity	NPC110657
0.8172	Intermediate Similarity	NPC218301
0.8172	Intermediate Similarity	NPC475416
0.8172	Intermediate Similarity	NPC150383
0.8172	Intermediate Similarity	NPC86266
0.8172	Intermediate Similarity	NPC212301
0.8163	Intermediate Similarity	NPC119601
0.8163	Intermediate Similarity	NPC136289
0.8163	Intermediate Similarity	NPC56498
0.8163	Intermediate Similarity	NPC281702
0.8163	Intermediate Similarity	NPC53222
0.8163	Intermediate Similarity	NPC308726
0.8152	Intermediate Similarity	NPC54689
0.8152	Intermediate Similarity	NPC474679
0.8152	Intermediate Similarity	NPC30522
0.8152	Intermediate Similarity	NPC470588
0.8152	Intermediate Similarity	NPC128496
0.8144	Intermediate Similarity	NPC205899
0.8144	Intermediate Similarity	NPC144660
0.8144	Intermediate Similarity	NPC83709
0.8144	Intermediate Similarity	NPC476274
0.8144	Intermediate Similarity	NPC299971
0.8137	Intermediate Similarity	NPC197428
0.8132	Intermediate Similarity	NPC167877
0.8132	Intermediate Similarity	NPC242468
0.8132	Intermediate Similarity	NPC68160
0.8132	Intermediate Similarity	NPC51700
0.8132	Intermediate Similarity	NPC102683
0.8132	Intermediate Similarity	NPC71507
0.8132	Intermediate Similarity	NPC18064
0.8132	Intermediate Similarity	NPC98442
0.8132	Intermediate Similarity	NPC293564
0.8132	Intermediate Similarity	NPC269360
0.8132	Intermediate Similarity	NPC142415
0.8132	Intermediate Similarity	NPC171203
0.8132	Intermediate Similarity	NPC130577
0.8132	Intermediate Similarity	NPC264005
0.8132	Intermediate Similarity	NPC88716
0.8132	Intermediate Similarity	NPC307426
0.8125	Intermediate Similarity	NPC320306
0.8125	Intermediate Similarity	NPC122294
0.8119	Intermediate Similarity	NPC94529
0.8119	Intermediate Similarity	NPC195708
0.8111	Intermediate Similarity	NPC16350
0.8111	Intermediate Similarity	NPC308041
0.8105	Intermediate Similarity	NPC241156
0.8105	Intermediate Similarity	NPC200702
0.8105	Intermediate Similarity	NPC259286
0.809	Intermediate Similarity	NPC278648
0.809	Intermediate Similarity	NPC471037
0.809	Intermediate Similarity	NPC476082
0.8085	Intermediate Similarity	NPC473690
0.8085	Intermediate Similarity	NPC477435
0.8085	Intermediate Similarity	NPC294263
0.8085	Intermediate Similarity	NPC224060
0.8085	Intermediate Similarity	NPC477436
0.8085	Intermediate Similarity	NPC287118
0.8085	Intermediate Similarity	NPC471902
0.8085	Intermediate Similarity	NPC244356
0.8085	Intermediate Similarity	NPC86368
0.8081	Intermediate Similarity	NPC55872
0.8081	Intermediate Similarity	NPC140723

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 NPC20388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1754
0.2-0.3	4111
0.3-0.4	2114
0.4-0.5	527
0.5-0.6	171
0.6-0.7	157
0.7-0.8	136
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD5328	Approved
0.8315	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD6079	Approved
0.81	Intermediate Similarity	NPD6675	Approved
0.81	Intermediate Similarity	NPD6402	Approved
0.81	Intermediate Similarity	NPD7128	Approved
0.81	Intermediate Similarity	NPD5739	Approved
0.8085	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD4786	Approved
0.7979	Intermediate Similarity	NPD8035	Phase 2
0.7979	Intermediate Similarity	NPD8034	Phase 2
0.7941	Intermediate Similarity	NPD6881	Approved
0.7941	Intermediate Similarity	NPD6899	Approved
0.7941	Intermediate Similarity	NPD7320	Approved
0.7864	Intermediate Similarity	NPD6372	Approved
0.7864	Intermediate Similarity	NPD6373	Approved
0.7843	Intermediate Similarity	NPD5701	Approved
0.7843	Intermediate Similarity	NPD5697	Approved
0.7826	Intermediate Similarity	NPD3618	Phase 1
0.7812	Intermediate Similarity	NPD7748	Approved
0.7789	Intermediate Similarity	NPD6411	Approved
0.7789	Intermediate Similarity	NPD7515	Phase 2
0.7788	Intermediate Similarity	NPD7102	Approved
0.7788	Intermediate Similarity	NPD7290	Approved
0.7788	Intermediate Similarity	NPD6883	Approved
0.7778	Intermediate Similarity	NPD3667	Approved
0.7767	Intermediate Similarity	NPD6011	Approved
0.7714	Intermediate Similarity	NPD6869	Approved
0.7714	Intermediate Similarity	NPD6847	Approved
0.7714	Intermediate Similarity	NPD6649	Approved
0.7714	Intermediate Similarity	NPD8130	Phase 1
0.7714	Intermediate Similarity	NPD6650	Approved
0.7714	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6617	Approved
0.7701	Intermediate Similarity	NPD6117	Approved
0.7692	Intermediate Similarity	NPD6013	Approved
0.7692	Intermediate Similarity	NPD6014	Approved
0.7692	Intermediate Similarity	NPD6012	Approved
0.7674	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5221	Approved
0.7653	Intermediate Similarity	NPD5222	Approved
0.7653	Intermediate Similarity	NPD4697	Phase 3
0.7653	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8297	Approved
0.7642	Intermediate Similarity	NPD6882	Approved
0.7634	Intermediate Similarity	NPD7334	Approved
0.7634	Intermediate Similarity	NPD6684	Approved
0.7634	Intermediate Similarity	NPD7521	Approved
0.7634	Intermediate Similarity	NPD5330	Approved
0.7634	Intermediate Similarity	NPD6409	Approved
0.7634	Intermediate Similarity	NPD7146	Approved
0.7614	Intermediate Similarity	NPD6116	Phase 1
0.7579	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6101	Approved
0.7576	Intermediate Similarity	NPD6084	Phase 2
0.7576	Intermediate Similarity	NPD4755	Approved
0.7576	Intermediate Similarity	NPD7902	Approved
0.7576	Intermediate Similarity	NPD5173	Approved
0.7576	Intermediate Similarity	NPD6083	Phase 2
0.7553	Intermediate Similarity	NPD3573	Approved
0.7551	Intermediate Similarity	NPD5695	Phase 3
0.7528	Intermediate Similarity	NPD6115	Approved
0.7528	Intermediate Similarity	NPD6697	Approved
0.7528	Intermediate Similarity	NPD6118	Approved
0.7528	Intermediate Similarity	NPD6114	Approved
0.7526	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.7474	Intermediate Similarity	NPD5737	Approved
0.7474	Intermediate Similarity	NPD6672	Approved
0.7474	Intermediate Similarity	NPD6903	Approved
0.7447	Intermediate Similarity	NPD5279	Phase 3
0.7431	Intermediate Similarity	NPD6868	Approved
0.7426	Intermediate Similarity	NPD4700	Approved
0.7426	Intermediate Similarity	NPD4696	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD5285	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.7426	Intermediate Similarity	NPD5286	Approved
0.7419	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD3666	Approved
0.7386	Intermediate Similarity	NPD3702	Approved
0.7358	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5223	Approved
0.7297	Intermediate Similarity	NPD6335	Approved
0.7283	Intermediate Similarity	NPD4139	Approved
0.7283	Intermediate Similarity	NPD4692	Approved
0.7282	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD5225	Approved
0.7282	Intermediate Similarity	NPD5211	Phase 2
0.7282	Intermediate Similarity	NPD4633	Approved
0.7282	Intermediate Similarity	NPD5224	Approved
0.7282	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD6274	Approved
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6098	Approved
0.7248	Intermediate Similarity	NPD4632	Approved
0.7241	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6008	Approved
0.7232	Intermediate Similarity	NPD7101	Approved
0.7232	Intermediate Similarity	NPD7100	Approved
0.7212	Intermediate Similarity	NPD4754	Approved
0.7212	Intermediate Similarity	NPD5174	Approved
0.7212	Intermediate Similarity	NPD5175	Approved
0.7207	Intermediate Similarity	NPD6317	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.72	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6942	Approved
0.7191	Intermediate Similarity	NPD7339	Approved
0.7191	Intermediate Similarity	NPD3703	Phase 2
0.7174	Intermediate Similarity	NPD7525	Registered
0.7174	Intermediate Similarity	NPD4748	Discontinued
0.7157	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD6313	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.7105	Intermediate Similarity	NPD6908	Approved
0.7105	Intermediate Similarity	NPD6909	Approved
0.7075	Intermediate Similarity	NPD4768	Approved
0.7075	Intermediate Similarity	NPD4767	Approved
0.7071	Intermediate Similarity	NPD6050	Approved
0.7071	Intermediate Similarity	NPD5281	Approved
0.7071	Intermediate Similarity	NPD5284	Approved
0.7065	Intermediate Similarity	NPD7645	Phase 2
0.7054	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6009	Approved
0.7053	Intermediate Similarity	NPD3668	Phase 3
0.7041	Intermediate Similarity	NPD6673	Approved
0.7041	Intermediate Similarity	NPD4753	Phase 2
0.7041	Intermediate Similarity	NPD6904	Approved
0.7041	Intermediate Similarity	NPD6080	Approved
0.7021	Intermediate Similarity	NPD4223	Phase 3
0.7021	Intermediate Similarity	NPD4221	Approved
0.7018	Intermediate Similarity	NPD6319	Approved
0.7011	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.7009	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.6983	Remote Similarity	NPD7604	Phase 2
0.6979	Remote Similarity	NPD5329	Approved
0.697	Remote Similarity	NPD5692	Phase 3
0.697	Remote Similarity	NPD5207	Approved
0.6957	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5983	Phase 2
0.6947	Remote Similarity	NPD4788	Approved
0.6944	Remote Similarity	NPD5128	Approved
0.6944	Remote Similarity	NPD4730	Approved
0.6944	Remote Similarity	NPD4729	Approved
0.6944	Remote Similarity	NPD5168	Approved
0.6939	Remote Similarity	NPD5208	Approved
0.6931	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7492	Approved
0.6907	Remote Similarity	NPD4694	Approved
0.6907	Remote Similarity	NPD5280	Approved
0.6907	Remote Similarity	NPD5690	Phase 2
0.6907	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5694	Approved
0.6891	Remote Similarity	NPD7736	Approved
0.6881	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4197	Approved
0.687	Remote Similarity	NPD6054	Approved
0.687	Remote Similarity	NPD6059	Approved
0.6869	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6336	Discontinued
0.6864	Remote Similarity	NPD6616	Approved
0.6854	Remote Similarity	NPD5777	Approved
0.6842	Remote Similarity	NPD6435	Approved
0.6833	Remote Similarity	NPD7319	Approved
0.6818	Remote Similarity	NPD5251	Approved
0.6818	Remote Similarity	NPD4634	Approved
0.6818	Remote Similarity	NPD5247	Approved
0.6818	Remote Similarity	NPD5135	Approved
0.6818	Remote Similarity	NPD5248	Approved
0.6818	Remote Similarity	NPD5249	Phase 3
0.6818	Remote Similarity	NPD5250	Approved
0.6818	Remote Similarity	NPD5169	Approved
0.6818	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8293	Discontinued
0.6807	Remote Similarity	NPD7078	Approved
0.6804	Remote Similarity	NPD1694	Approved
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5217	Approved
0.6757	Remote Similarity	NPD5216	Approved
0.6757	Remote Similarity	NPD5215	Approved
0.6757	Remote Similarity	NPD5127	Approved
0.6752	Remote Similarity	NPD6370	Approved
0.6744	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4789	Approved
0.6742	Remote Similarity	NPD4244	Approved
0.6742	Remote Similarity	NPD4245	Approved
0.6735	Remote Similarity	NPD4693	Phase 3
0.6735	Remote Similarity	NPD4689	Approved
0.6735	Remote Similarity	NPD4688	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