NPASS Compound

Structure

NPC159046 OpenBabel07101718292D 33 36 0 0 1 0 0 0 0 0999 V2000 4.8126 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 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 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 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 3.8344 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 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 -0.5000 0.0000 C 0 0 0 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 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5909 3.0032 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 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 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 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 20 10 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 6 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 23 30 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 1 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 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	511.671
LogP:	6.97
LogD:	4.732
LogS:	-3.834
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	4.708
Fsp3:	0.833
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:	-5.285
MDCK Permeability:	1.1620189070526976e-05
Pgp-inhibitor:	0.506
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	92.10028839111328%
Volume Distribution (VD):	0.844
Pgp-substrate:	2.582407236099243%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.236
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.745
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.677

ADMET: Excretion

Clearance (CL):	19.583
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.601
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.602
Carcinogencity:	0.346
Eye Corrosion:	0.006
Eye Irritation:	0.024
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: NPC159046

Natural Product ID:	NPC159046
*Common Name:**	3-Beta-Hydroxy-8,24-Diene-Tirucallic Acid
IUPAC Name:	(2S)-2-[(3S,5R,10S,13S,14S,17S)-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]-6-methylhept-5-enoic acid
Synonyms:
Standard InCHIKey:	NBSBUIQBEPROBM-VGYIVZNUSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24-25,31H,8,10-18H2,1-7H3,(H,32,33)/t20-,21-,24-,25-,28+,29-,30+/m0/s1
SMILES:	CC(=CCC[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(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289098
PubChem CID:	90644334
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
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24844534]

☑ 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	3
Others	3

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Activity	=	82.3	%	PMID[465767]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Activity	=	83.4	%	PMID[465767]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000.0	nM	PMID[465767]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10000.0	nM	PMID[465767]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	29.2	%	PMID[465767]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	1200.0	nM	PMID[465767]

☑ 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 NPC159046 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	155
0.1-0.2	1043
0.2-0.3	4914
0.3-0.4	15001
0.4-0.5	7675
0.5-0.6	6028
0.6-0.7	5083
0.7-0.8	2343
0.8-0.85	308
0.85-0.9	103
0.9-0.95	35
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233836
1.0	High Similarity	NPC187376
0.9877	High Similarity	NPC55309
0.9877	High Similarity	NPC28252
0.9759	High Similarity	NPC77168
0.9759	High Similarity	NPC102414
0.9759	High Similarity	NPC84271
0.9756	High Similarity	NPC474684
0.9756	High Similarity	NPC142361
0.9639	High Similarity	NPC242864
0.9524	High Similarity	NPC474704
0.9524	High Similarity	NPC475921
0.9412	High Similarity	NPC148414
0.9412	High Similarity	NPC175628
0.9412	High Similarity	NPC469400
0.9412	High Similarity	NPC111585
0.9398	High Similarity	NPC155011
0.9398	High Similarity	NPC94755
0.931	High Similarity	NPC469406
0.9302	High Similarity	NPC189520
0.9302	High Similarity	NPC26888
0.9302	High Similarity	NPC297265
0.9302	High Similarity	NPC23434
0.9294	High Similarity	NPC474889
0.9205	High Similarity	NPC45324
0.9205	High Similarity	NPC162001
0.9205	High Similarity	NPC222845
0.9195	High Similarity	NPC470376
0.9195	High Similarity	NPC470375
0.9195	High Similarity	NPC470224
0.9186	High Similarity	NPC471896
0.9176	High Similarity	NPC471722
0.9167	High Similarity	NPC72133
0.9157	High Similarity	NPC165064
0.9101	High Similarity	NPC173272
0.9091	High Similarity	NPC166906
0.908	High Similarity	NPC110657
0.908	High Similarity	NPC212301
0.908	High Similarity	NPC86266
0.907	High Similarity	NPC86319
0.907	High Similarity	NPC275740
0.907	High Similarity	NPC128496
0.9024	High Similarity	NPC38350
0.9024	High Similarity	NPC201912
0.9024	High Similarity	NPC473420
0.8989	High Similarity	NPC317586
0.8989	High Similarity	NPC69548
0.8989	High Similarity	NPC184848
0.8989	High Similarity	NPC470016
0.8989	High Similarity	NPC48330
0.8977	High Similarity	NPC170220
0.8977	High Similarity	NPC107674
0.8977	High Similarity	NPC141497
0.8977	High Similarity	NPC477855
0.8966	High Similarity	NPC191684
0.8966	High Similarity	NPC20388
0.8953	High Similarity	NPC471724
0.8953	High Similarity	NPC143767
0.8953	High Similarity	NPC131470
0.8941	High Similarity	NPC73038
0.8941	High Similarity	NPC325594
0.8929	High Similarity	NPC59453
0.8929	High Similarity	NPC221758
0.8929	High Similarity	NPC473246
0.8916	High Similarity	NPC260956
0.8916	High Similarity	NPC73882
0.8901	High Similarity	NPC477813
0.8901	High Similarity	NPC186810
0.8901	High Similarity	NPC48647
0.8889	High Similarity	NPC120708
0.8889	High Similarity	NPC328162
0.8889	High Similarity	NPC96859
0.8889	High Similarity	NPC305483
0.8876	High Similarity	NPC49670
0.8851	High Similarity	NPC54689
0.8837	High Similarity	NPC98442
0.8837	High Similarity	NPC102683
0.8837	High Similarity	NPC51700
0.8837	High Similarity	NPC71507
0.8837	High Similarity	NPC242468
0.8837	High Similarity	NPC312215
0.8837	High Similarity	NPC88716
0.8837	High Similarity	NPC475740
0.8837	High Similarity	NPC130577
0.8837	High Similarity	NPC293564
0.8837	High Similarity	NPC68160
0.8837	High Similarity	NPC96496
0.8837	High Similarity	NPC142415
0.8837	High Similarity	NPC307426
0.8837	High Similarity	NPC171203
0.8837	High Similarity	NPC18064
0.8824	High Similarity	NPC470574
0.8824	High Similarity	NPC294438
0.8824	High Similarity	NPC264317
0.8824	High Similarity	NPC474083
0.881	High Similarity	NPC83569
0.881	High Similarity	NPC69279
0.8795	High Similarity	NPC147066
0.8791	High Similarity	NPC108078
0.8791	High Similarity	NPC320306
0.878	High Similarity	NPC477371
0.8778	High Similarity	NPC279974
0.8765	High Similarity	NPC214570
0.8764	High Similarity	NPC66429
0.8764	High Similarity	NPC69454
0.8764	High Similarity	NPC152897
0.875	High Similarity	NPC44240
0.875	High Similarity	NPC183283
0.8736	High Similarity	NPC328539
0.8736	High Similarity	NPC17733
0.8736	High Similarity	NPC474512
0.8736	High Similarity	NPC181225
0.8736	High Similarity	NPC473242
0.8736	High Similarity	NPC52169
0.8736	High Similarity	NPC193360
0.8736	High Similarity	NPC470629
0.8736	High Similarity	NPC246708
0.8736	High Similarity	NPC40552
0.8736	High Similarity	NPC290690
0.8736	High Similarity	NPC182797
0.8736	High Similarity	NPC294480
0.8721	High Similarity	NPC474970
0.8721	High Similarity	NPC72638
0.8721	High Similarity	NPC145879
0.8721	High Similarity	NPC474732
0.8721	High Similarity	NPC475022
0.8721	High Similarity	NPC51014
0.8721	High Similarity	NPC222613
0.8721	High Similarity	NPC118648
0.8721	High Similarity	NPC474778
0.8721	High Similarity	NPC2783
0.8721	High Similarity	NPC474733
0.8721	High Similarity	NPC31564
0.8721	High Similarity	NPC212843
0.8721	High Similarity	NPC12774
0.8706	High Similarity	NPC171789
0.8706	High Similarity	NPC85774
0.8706	High Similarity	NPC214043
0.8706	High Similarity	NPC82902
0.869	High Similarity	NPC151519
0.8681	High Similarity	NPC472941
0.8681	High Similarity	NPC456
0.8667	High Similarity	NPC159410
0.8667	High Similarity	NPC471720
0.8659	High Similarity	NPC275910
0.8652	High Similarity	NPC272746
0.8652	High Similarity	NPC301244
0.8652	High Similarity	NPC212948
0.8652	High Similarity	NPC233116
0.8652	High Similarity	NPC63748
0.8652	High Similarity	NPC154101
0.8642	High Similarity	NPC202642
0.8642	High Similarity	NPC46160
0.8642	High Similarity	NPC73875
0.8636	High Similarity	NPC214387
0.8636	High Similarity	NPC274330
0.8636	High Similarity	NPC472240
0.8636	High Similarity	NPC270768
0.8636	High Similarity	NPC474972
0.8636	High Similarity	NPC262858
0.8636	High Similarity	NPC127689
0.8636	High Similarity	NPC234346
0.8636	High Similarity	NPC59263
0.8636	High Similarity	NPC143232
0.8636	High Similarity	NPC25906
0.8636	High Similarity	NPC198664
0.8636	High Similarity	NPC95246
0.8636	High Similarity	NPC32830
0.8636	High Similarity	NPC31985
0.8636	High Similarity	NPC61543
0.8636	High Similarity	NPC474245
0.8636	High Similarity	NPC1015
0.8636	High Similarity	NPC263393
0.8636	High Similarity	NPC64872
0.8636	High Similarity	NPC161751
0.8636	High Similarity	NPC130520
0.8636	High Similarity	NPC121798
0.8636	High Similarity	NPC225585
0.8636	High Similarity	NPC473999
0.8636	High Similarity	NPC290972
0.8636	High Similarity	NPC470588
0.8636	High Similarity	NPC309603
0.8636	High Similarity	NPC293048
0.8621	High Similarity	NPC138756
0.8621	High Similarity	NPC269360
0.8621	High Similarity	NPC264005
0.8621	High Similarity	NPC33768
0.8621	High Similarity	NPC58063
0.8621	High Similarity	NPC167877
0.8617	High Similarity	NPC293753
0.8617	High Similarity	NPC234892
0.8605	High Similarity	NPC474218
0.8605	High Similarity	NPC471224
0.8602	High Similarity	NPC327431
0.8602	High Similarity	NPC316964
0.8588	High Similarity	NPC278648
0.8588	High Similarity	NPC476082
0.8587	High Similarity	NPC43747
0.8571	High Similarity	NPC255809
0.8571	High Similarity	NPC173875

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 NPC159046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1399
0.2-0.3	4047
0.3-0.4	2404
0.4-0.5	643
0.5-0.6	195
0.6-0.7	149
0.7-0.8	160
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD4786	Approved
0.8851	High Similarity	NPD5328	Approved
0.8824	High Similarity	NPD7520	Clinical (unspecified phase)
0.8721	High Similarity	NPD3618	Phase 1
0.869	High Similarity	NPD3667	Approved
0.8652	High Similarity	NPD6079	Approved
0.8556	High Similarity	NPD6399	Phase 3
0.8444	Intermediate Similarity	NPD7515	Phase 2
0.8352	Intermediate Similarity	NPD4202	Approved
0.8295	Intermediate Similarity	NPD5279	Phase 3
0.8276	Intermediate Similarity	NPD3666	Approved
0.8276	Intermediate Similarity	NPD3133	Approved
0.8276	Intermediate Similarity	NPD3665	Phase 1
0.8163	Intermediate Similarity	NPD7128	Approved
0.8163	Intermediate Similarity	NPD6402	Approved
0.8163	Intermediate Similarity	NPD5739	Approved
0.8163	Intermediate Similarity	NPD6675	Approved
0.809	Intermediate Similarity	NPD6684	Approved
0.809	Intermediate Similarity	NPD7146	Approved
0.809	Intermediate Similarity	NPD7521	Approved
0.809	Intermediate Similarity	NPD7334	Approved
0.809	Intermediate Similarity	NPD5330	Approved
0.809	Intermediate Similarity	NPD6409	Approved
0.8085	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD5222	Approved
0.8085	Intermediate Similarity	NPD4697	Phase 3
0.8085	Intermediate Similarity	NPD5221	Approved
0.8072	Intermediate Similarity	NPD7339	Approved
0.8072	Intermediate Similarity	NPD6942	Approved
0.8065	Intermediate Similarity	NPD7748	Approved
0.8043	Intermediate Similarity	NPD8035	Phase 2
0.8043	Intermediate Similarity	NPD8034	Phase 2
0.8023	Intermediate Similarity	NPD7525	Registered
0.8	Intermediate Similarity	NPD5173	Approved
0.8	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD4755	Approved
0.8	Intermediate Similarity	NPD6881	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.7979	Intermediate Similarity	NPD5695	Phase 3
0.7976	Intermediate Similarity	NPD6117	Approved
0.7952	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6372	Approved
0.7921	Intermediate Similarity	NPD6373	Approved
0.7917	Intermediate Similarity	NPD7638	Approved
0.7912	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6672	Approved
0.7912	Intermediate Similarity	NPD5737	Approved
0.7912	Intermediate Similarity	NPD6903	Approved
0.79	Intermediate Similarity	NPD5701	Approved
0.79	Intermediate Similarity	NPD5697	Approved
0.7882	Intermediate Similarity	NPD6116	Phase 1
0.7865	Intermediate Similarity	NPD3668	Phase 3
0.7849	Intermediate Similarity	NPD5281	Approved
0.7849	Intermediate Similarity	NPD5284	Approved
0.7843	Intermediate Similarity	NPD7290	Approved
0.7843	Intermediate Similarity	NPD7102	Approved
0.7843	Intermediate Similarity	NPD6883	Approved
0.7841	Intermediate Similarity	NPD4221	Approved
0.7841	Intermediate Similarity	NPD4223	Phase 3
0.7835	Intermediate Similarity	NPD4700	Approved
0.7835	Intermediate Similarity	NPD4696	Approved
0.7835	Intermediate Similarity	NPD7639	Approved
0.7835	Intermediate Similarity	NPD7640	Approved
0.7835	Intermediate Similarity	NPD5286	Approved
0.7835	Intermediate Similarity	NPD5285	Approved
0.7826	Intermediate Similarity	NPD4753	Phase 2
0.7822	Intermediate Similarity	NPD6011	Approved
0.7812	Intermediate Similarity	NPD7902	Approved
0.7791	Intermediate Similarity	NPD6118	Approved
0.7791	Intermediate Similarity	NPD6697	Approved
0.7791	Intermediate Similarity	NPD6115	Approved
0.7791	Intermediate Similarity	NPD6114	Approved
0.7778	Intermediate Similarity	NPD5329	Approved
0.7767	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD6869	Approved
0.7767	Intermediate Similarity	NPD6847	Approved
0.7767	Intermediate Similarity	NPD6649	Approved
0.7767	Intermediate Similarity	NPD8130	Phase 1
0.7767	Intermediate Similarity	NPD6650	Approved
0.7767	Intermediate Similarity	NPD6617	Approved
0.7765	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5223	Approved
0.7745	Intermediate Similarity	NPD6013	Approved
0.7745	Intermediate Similarity	NPD6014	Approved
0.7745	Intermediate Similarity	NPD6012	Approved
0.7692	Intermediate Similarity	NPD6882	Approved
0.7692	Intermediate Similarity	NPD4694	Approved
0.7692	Intermediate Similarity	NPD6098	Approved
0.7692	Intermediate Similarity	NPD5690	Phase 2
0.7692	Intermediate Similarity	NPD8297	Approved
0.7692	Intermediate Similarity	NPD5280	Approved
0.7677	Intermediate Similarity	NPD5211	Phase 2
0.7677	Intermediate Similarity	NPD5225	Approved
0.7677	Intermediate Similarity	NPD5226	Approved
0.7677	Intermediate Similarity	NPD5224	Approved
0.7677	Intermediate Similarity	NPD4633	Approved
0.7667	Intermediate Similarity	NPD4197	Approved
0.766	Intermediate Similarity	NPD6411	Approved
0.7604	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5175	Approved
0.76	Intermediate Similarity	NPD5174	Approved
0.76	Intermediate Similarity	NPD4754	Approved
0.7586	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4788	Approved
0.7551	Intermediate Similarity	NPD5696	Approved
0.7528	Intermediate Similarity	NPD4692	Approved
0.7528	Intermediate Similarity	NPD4139	Approved
0.7525	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD7645	Phase 2
0.75	Intermediate Similarity	NPD7900	Approved
0.7477	Intermediate Similarity	NPD6868	Approved
0.7474	Intermediate Similarity	NPD6050	Approved
0.7453	Intermediate Similarity	NPD4632	Approved
0.7451	Intermediate Similarity	NPD4767	Approved
0.7451	Intermediate Similarity	NPD4768	Approved
0.7447	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6673	Approved
0.7447	Intermediate Similarity	NPD6080	Approved
0.7447	Intermediate Similarity	NPD6101	Approved
0.7447	Intermediate Similarity	NPD6904	Approved
0.7423	Intermediate Similarity	NPD5210	Approved
0.7423	Intermediate Similarity	NPD4629	Approved
0.7416	Intermediate Similarity	NPD4748	Discontinued
0.7407	Intermediate Similarity	NPD7115	Discovery
0.7386	Intermediate Similarity	NPD3617	Approved
0.7368	Intermediate Similarity	NPD5692	Phase 3
0.7368	Intermediate Similarity	NPD5207	Approved
0.734	Intermediate Similarity	NPD5208	Approved
0.7339	Intermediate Similarity	NPD6335	Approved
0.7326	Intermediate Similarity	NPD6926	Approved
0.7326	Intermediate Similarity	NPD6924	Approved
0.7326	Intermediate Similarity	NPD5733	Approved
0.732	Intermediate Similarity	NPD6001	Approved
0.7315	Intermediate Similarity	NPD6274	Approved
0.7308	Intermediate Similarity	NPD4729	Approved
0.7308	Intermediate Similarity	NPD5128	Approved
0.7308	Intermediate Similarity	NPD5168	Approved
0.7308	Intermediate Similarity	NPD4730	Approved
0.73	Intermediate Similarity	NPD6404	Discontinued
0.7294	Intermediate Similarity	NPD4243	Approved
0.7292	Intermediate Similarity	NPD5694	Approved
0.7282	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD7101	Approved
0.7273	Intermediate Similarity	NPD7100	Approved
0.7263	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6317	Approved
0.7248	Intermediate Similarity	NPD6009	Approved
0.7234	Intermediate Similarity	NPD3573	Approved
0.7188	Intermediate Similarity	NPD4096	Approved
0.7182	Intermediate Similarity	NPD6314	Approved
0.7182	Intermediate Similarity	NPD6313	Approved
0.7176	Intermediate Similarity	NPD4747	Approved
0.7174	Intermediate Similarity	NPD5362	Discontinued
0.717	Intermediate Similarity	NPD4634	Approved
0.717	Intermediate Similarity	NPD5251	Approved
0.717	Intermediate Similarity	NPD5250	Approved
0.717	Intermediate Similarity	NPD5169	Approved
0.717	Intermediate Similarity	NPD5247	Approved
0.717	Intermediate Similarity	NPD5248	Approved
0.717	Intermediate Similarity	NPD5249	Phase 3
0.717	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5135	Approved
0.7159	Intermediate Similarity	NPD6933	Approved
0.7157	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD6909	Approved
0.7143	Intermediate Similarity	NPD6908	Approved
0.7126	Intermediate Similarity	NPD4784	Approved
0.7126	Intermediate Similarity	NPD4785	Approved
0.7126	Intermediate Similarity	NPD4687	Approved
0.7113	Intermediate Similarity	NPD5693	Phase 1
0.7111	Intermediate Similarity	NPD4195	Approved
0.7103	Intermediate Similarity	NPD5215	Approved
0.7103	Intermediate Similarity	NPD5127	Approved
0.7103	Intermediate Similarity	NPD5216	Approved
0.7103	Intermediate Similarity	NPD5217	Approved
0.7093	Intermediate Similarity	NPD7152	Approved
0.7093	Intermediate Similarity	NPD7150	Approved
0.7093	Intermediate Similarity	NPD5276	Approved
0.7093	Intermediate Similarity	NPD7151	Approved
0.7083	Intermediate Similarity	NPD6051	Approved
0.7059	Intermediate Similarity	NPD6922	Approved
0.7059	Intermediate Similarity	NPD6923	Approved
0.7059	Intermediate Similarity	NPD4137	Phase 3
0.7054	Intermediate Similarity	NPD6319	Approved
0.7053	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6412	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