NPASS Compound

Structure

NPC470922 OpenBabel07101719122D 42 46 0 0 1 0 0 0 0 0999 V2000 7.6527 2.9197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4680 2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6016 5.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7799 0.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3460 1.8405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 1.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9471 3.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7586 2.0268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9525 1.9108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1251 -0.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1441 3.2301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5616 -0.7730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3072 4.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9525 0.9554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8001 0.7173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1251 0.4777 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1251 2.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2977 -0.9554 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9229 0.0404 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3921 0.1044 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1942 1.0433 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2977 1.9108 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3728 4.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7346 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 0.4777 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5552 1.4123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2977 0.9554 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8496 2.3212 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4702 -0.4777 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5616 0.7730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1251 3.3440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 1.9978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 2.3885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7329 5.0480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6288 0.1140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1952 0.7028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9407 2.6156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1793 1.3762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0784 3.4296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6926 -0.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6865 1.0133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 7 13 2 0 0 0 0 8 28 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 28 1 0 0 0 0 11 39 1 0 0 0 0 12 40 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 27 1 6 0 0 0 17 22 1 0 0 0 0 17 31 2 0 0 0 0 18 29 1 6 0 0 0 18 41 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 24 1 0 0 0 0 20 42 1 1 0 0 0 21 30 1 6 0 0 0 21 32 1 0 0 0 0 22 27 1 6 0 0 0 22 33 1 0 0 0 0 23 34 2 0 0 0 0 23 39 1 0 0 0 0 24 35 2 0 0 0 0 24 41 1 0 0 0 0 25 27 1 6 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 36 2 0 0 0 0 26 42 1 0 0 0 0 27 6 1 6 0 0 0 28 37 1 0 0 0 0 29 12 1 1 0 0 0 30 38 1 1 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.24
Volume:	571.681
LogP:	1.633
LogD:	0.952
LogS:	-4.071
# Rotatable Bonds:	8
TPSA:	182.96
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	6.96
Fsp3:	0.7
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.42
MDCK Permeability:	6.75880946801044e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.679
Human Intestinal Absorption (HIA):	0.188
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	62.07481002807617%
Volume Distribution (VD):	0.634
Pgp-substrate:	35.35458755493164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.247
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	2.794
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.807
AMES Toxicity:	0.14
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.624
Skin Sensitization:	0.186
Carcinogencity:	0.222
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC470922

Natural Product ID:	NPC470922
*Common Name:**	Altissinol A
IUPAC Name:	n.a.
Synonyms:	Altissinol A
Standard InCHIKey:	SVVNBEJHMASBLJ-HARZPQNQSA-N
Standard InCHI:	InChI=1S/C30H38O12/c1-7-13(3)23(34)39-11-28(37,8-2)26(36)42-20-19-15(5)21(32)30(38)25-27(6)16(14(4)9-17(31)22(27)33)10-18(41-24(20)35)29(19,25)12-40-30/h7,9,16,18-22,25,32-33,37-38H,5,8,10-12H2,1-4,6H3/b13-7-/t16-,18+,19+,20+,21+,22+,25+,27+,28?,29-,30+/m0/s1
SMILES:	C/C=C(C(=O)OCC(C(=O)O[C@H]1C(=O)O[C@H]2[C@]34[C@@H]1C(=C)[C@@H](O)[C@]([C@@H]4[C@@]1([C@@H](C2)C(=CC(=O)[C@H]1O)C)C)(OC3)O)(CC)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2314663
PubChem CID:	71519983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[482300]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	280.0	nM	PMID[482300]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	370.0	nM	PMID[482300]

☑ 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 NPC470922 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	262
0.1-0.2	1462
0.2-0.3	3993
0.3-0.4	6756
0.4-0.5	10745
0.5-0.6	9152
0.6-0.7	6017
0.7-0.8	3549
0.8-0.85	549
0.85-0.9	143
0.9-0.95	64
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9649	High Similarity	NPC109607
0.9649	High Similarity	NPC107338
0.9561	High Similarity	NPC475775
0.9561	High Similarity	NPC476529
0.9474	High Similarity	NPC297179
0.9402	High Similarity	NPC67251
0.9386	High Similarity	NPC473968
0.9322	High Similarity	NPC476729
0.9322	High Similarity	NPC24651
0.931	High Similarity	NPC112038
0.9298	High Similarity	NPC152199
0.9298	High Similarity	NPC470628
0.9298	High Similarity	NPC474046
0.9298	High Similarity	NPC235539
0.9298	High Similarity	NPC134869
0.9298	High Similarity	NPC259306
0.9237	High Similarity	NPC18945
0.9237	High Similarity	NPC265557
0.9237	High Similarity	NPC91693
0.9237	High Similarity	NPC105926
0.9211	High Similarity	NPC18547
0.9211	High Similarity	NPC470919
0.9211	High Similarity	NPC469877
0.9211	High Similarity	NPC474906
0.9153	High Similarity	NPC312833
0.9138	High Similarity	NPC188667
0.9138	High Similarity	NPC204552
0.9123	High Similarity	NPC51978
0.9068	High Similarity	NPC470779
0.906	High Similarity	NPC469488
0.9052	High Similarity	NPC473590
0.9035	High Similarity	NPC302146
0.9035	High Similarity	NPC289312
0.9035	High Similarity	NPC11252
0.8974	High Similarity	NPC17772
0.8974	High Similarity	NPC251310
0.8974	High Similarity	NPC470776
0.8968	High Similarity	NPC596
0.8968	High Similarity	NPC295885
0.8968	High Similarity	NPC140045
0.8966	High Similarity	NPC251236
0.8966	High Similarity	NPC40632
0.8966	High Similarity	NPC96312
0.8966	High Similarity	NPC474734
0.8966	High Similarity	NPC328374
0.8952	High Similarity	NPC168879
0.8952	High Similarity	NPC478151
0.8947	High Similarity	NPC201992
0.8908	High Similarity	NPC477046
0.8908	High Similarity	NPC102822
0.8898	High Similarity	NPC470777
0.8889	High Similarity	NPC470775
0.8889	High Similarity	NPC474654
0.8889	High Similarity	NPC141215
0.8889	High Similarity	NPC287343
0.8889	High Similarity	NPC471089
0.8889	High Similarity	NPC97908
0.8889	High Similarity	NPC176513
0.8889	High Similarity	NPC470854
0.8889	High Similarity	NPC122033
0.8889	High Similarity	NPC251998
0.8889	High Similarity	NPC190065
0.8879	High Similarity	NPC473798
0.8871	High Similarity	NPC478153
0.8871	High Similarity	NPC102316
0.8871	High Similarity	NPC478152
0.8871	High Similarity	NPC478150
0.8871	High Similarity	NPC478154
0.887	High Similarity	NPC269530
0.8852	High Similarity	NPC470780
0.881	High Similarity	NPC262813
0.8793	High Similarity	NPC49451
0.8793	High Similarity	NPC7921
0.8793	High Similarity	NPC208998
0.879	High Similarity	NPC301639
0.879	High Similarity	NPC45346
0.879	High Similarity	NPC475377
0.879	High Similarity	NPC478065
0.879	High Similarity	NPC476852
0.879	High Similarity	NPC477197
0.879	High Similarity	NPC475167
0.879	High Similarity	NPC172374
0.879	High Similarity	NPC478155
0.879	High Similarity	NPC173435
0.879	High Similarity	NPC134914
0.879	High Similarity	NPC262796
0.879	High Similarity	NPC25998
0.879	High Similarity	NPC478064
0.879	High Similarity	NPC329993
0.879	High Similarity	NPC264566
0.879	High Similarity	NPC476074
0.878	High Similarity	NPC476859
0.8772	High Similarity	NPC143706
0.8772	High Similarity	NPC472534
0.877	High Similarity	NPC225049
0.8739	High Similarity	NPC473636
0.8739	High Similarity	NPC122971
0.8739	High Similarity	NPC77689
0.8739	High Similarity	NPC268958
0.8729	High Similarity	NPC477116
0.8729	High Similarity	NPC134430
0.8729	High Similarity	NPC27999
0.8729	High Similarity	NPC470778
0.8729	High Similarity	NPC146432
0.872	High Similarity	NPC471855
0.871	High Similarity	NPC477196
0.871	High Similarity	NPC477076
0.871	High Similarity	NPC477079
0.871	High Similarity	NPC470913
0.871	High Similarity	NPC477077
0.871	High Similarity	NPC476851
0.8699	High Similarity	NPC470882
0.8699	High Similarity	NPC476008
0.8684	High Similarity	NPC293850
0.8678	High Similarity	NPC269642
0.8644	High Similarity	NPC16081
0.8644	High Similarity	NPC213084
0.8644	High Similarity	NPC190185
0.8644	High Similarity	NPC173686
0.8644	High Similarity	NPC89929
0.864	High Similarity	NPC476855
0.8632	High Similarity	NPC94509
0.8632	High Similarity	NPC25909
0.8629	High Similarity	NPC477078
0.8629	High Similarity	NPC311534
0.8629	High Similarity	NPC473620
0.8629	High Similarity	NPC477194
0.8629	High Similarity	NPC477075
0.8629	High Similarity	NPC329923
0.8629	High Similarity	NPC477191
0.8629	High Similarity	NPC477192
0.8629	High Similarity	NPC477193
0.8629	High Similarity	NPC475281
0.8621	High Similarity	NPC146945
0.8621	High Similarity	NPC171888
0.8618	High Similarity	NPC477745
0.8618	High Similarity	NPC293112
0.8607	High Similarity	NPC469789
0.8594	High Similarity	NPC243014
0.8583	High Similarity	NPC211093
0.8583	High Similarity	NPC473839
0.8571	High Similarity	NPC476193
0.8571	High Similarity	NPC473918
0.8571	High Similarity	NPC100390
0.8571	High Similarity	NPC71391
0.8571	High Similarity	NPC178264
0.8571	High Similarity	NPC254614
0.8571	High Similarity	NPC192765
0.8571	High Similarity	NPC476776
0.8571	High Similarity	NPC477195
0.8571	High Similarity	NPC474483
0.8571	High Similarity	NPC46823
0.8571	High Similarity	NPC309433
0.8571	High Similarity	NPC277212
0.8571	High Similarity	NPC30279
0.8571	High Similarity	NPC475809
0.856	High Similarity	NPC141600
0.856	High Similarity	NPC280029
0.856	High Similarity	NPC11577
0.856	High Similarity	NPC82380
0.856	High Similarity	NPC305793
0.856	High Similarity	NPC252289
0.856	High Similarity	NPC273878
0.856	High Similarity	NPC107536
0.856	High Similarity	NPC88311
0.856	High Similarity	NPC9470
0.856	High Similarity	NPC115656
0.856	High Similarity	NPC97918
0.856	High Similarity	NPC244296
0.856	High Similarity	NPC252657
0.856	High Similarity	NPC471407
0.856	High Similarity	NPC269484
0.856	High Similarity	NPC470912
0.856	High Similarity	NPC476854
0.856	High Similarity	NPC472267
0.856	High Similarity	NPC1314
0.856	High Similarity	NPC476966
0.856	High Similarity	NPC470518
0.8559	High Similarity	NPC243354
0.8559	High Similarity	NPC268238
0.8559	High Similarity	NPC323821
0.8559	High Similarity	NPC45218
0.8559	High Similarity	NPC299849
0.8559	High Similarity	NPC143268
0.8548	High Similarity	NPC42399
0.8548	High Similarity	NPC473265
0.8547	High Similarity	NPC474516
0.8547	High Similarity	NPC317687
0.8537	High Similarity	NPC172154
0.8537	High Similarity	NPC318135
0.8537	High Similarity	NPC8369
0.8537	High Similarity	NPC81736
0.8534	High Similarity	NPC5103
0.8534	High Similarity	NPC474567
0.8525	High Similarity	NPC470265
0.8525	High Similarity	NPC23786
0.8512	High Similarity	NPC476961
0.8512	High Similarity	NPC478051
0.8512	High Similarity	NPC48692
0.8504	High Similarity	NPC225791

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 NPC470922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	1651
0.2-0.3	3562
0.3-0.4	2351
0.4-0.5	751
0.5-0.6	333
0.6-0.7	166
0.7-0.8	103
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8306	Intermediate Similarity	NPD8328	Phase 3
0.824	Intermediate Similarity	NPD7492	Approved
0.8211	Intermediate Similarity	NPD6054	Approved
0.8211	Intermediate Similarity	NPD6319	Approved
0.8189	Intermediate Similarity	NPD7736	Approved
0.8175	Intermediate Similarity	NPD6616	Approved
0.8125	Intermediate Similarity	NPD7319	Approved
0.8115	Intermediate Similarity	NPD7115	Discovery
0.811	Intermediate Similarity	NPD7078	Approved
0.808	Intermediate Similarity	NPD6370	Approved
0.8065	Intermediate Similarity	NPD6059	Approved
0.8051	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD6686	Approved
0.8031	Intermediate Similarity	NPD7507	Approved
0.8	Intermediate Similarity	NPD6016	Approved
0.8	Intermediate Similarity	NPD6015	Approved
0.7969	Intermediate Similarity	NPD8293	Discontinued
0.7967	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5988	Approved
0.7934	Intermediate Similarity	NPD8297	Approved
0.7934	Intermediate Similarity	NPD6882	Approved
0.7857	Intermediate Similarity	NPD8516	Approved
0.7857	Intermediate Similarity	NPD8513	Phase 3
0.7857	Intermediate Similarity	NPD8517	Approved
0.7857	Intermediate Similarity	NPD8515	Approved
0.7826	Intermediate Similarity	NPD4225	Approved
0.7823	Intermediate Similarity	NPD6009	Approved
0.775	Intermediate Similarity	NPD6881	Approved
0.775	Intermediate Similarity	NPD6899	Approved
0.7731	Intermediate Similarity	NPD6675	Approved
0.7731	Intermediate Similarity	NPD7128	Approved
0.7731	Intermediate Similarity	NPD6402	Approved
0.7731	Intermediate Similarity	NPD5739	Approved
0.7724	Intermediate Similarity	NPD4632	Approved
0.7705	Intermediate Similarity	NPD6649	Approved
0.7705	Intermediate Similarity	NPD6650	Approved
0.7686	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD6373	Approved
0.7686	Intermediate Similarity	NPD6372	Approved
0.7667	Intermediate Similarity	NPD5697	Approved
0.7623	Intermediate Similarity	NPD7102	Approved
0.7623	Intermediate Similarity	NPD7290	Approved
0.7623	Intermediate Similarity	NPD6883	Approved
0.7603	Intermediate Similarity	NPD7320	Approved
0.7561	Intermediate Similarity	NPD6869	Approved
0.7561	Intermediate Similarity	NPD6847	Approved
0.7561	Intermediate Similarity	NPD8130	Phase 1
0.7561	Intermediate Similarity	NPD6617	Approved
0.7559	Intermediate Similarity	NPD7516	Approved
0.7541	Intermediate Similarity	NPD6012	Approved
0.7541	Intermediate Similarity	NPD6014	Approved
0.7541	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6013	Approved
0.7521	Intermediate Similarity	NPD5701	Approved
0.7521	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD6033	Approved
0.748	Intermediate Similarity	NPD4634	Approved
0.748	Intermediate Similarity	NPD7328	Approved
0.748	Intermediate Similarity	NPD7327	Approved
0.748	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7604	Phase 2
0.7459	Intermediate Similarity	NPD6011	Approved
0.7458	Intermediate Similarity	NPD7639	Approved
0.7458	Intermediate Similarity	NPD7640	Approved
0.7442	Intermediate Similarity	NPD8033	Approved
0.7442	Intermediate Similarity	NPD6921	Approved
0.7442	Intermediate Similarity	NPD7503	Approved
0.7442	Intermediate Similarity	NPD5983	Phase 2
0.7424	Intermediate Similarity	NPD8074	Phase 3
0.7419	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7638	Approved
0.7364	Intermediate Similarity	NPD8294	Approved
0.7364	Intermediate Similarity	NPD8377	Approved
0.7348	Intermediate Similarity	NPD6336	Discontinued
0.7333	Intermediate Similarity	NPD5211	Phase 2
0.7308	Intermediate Similarity	NPD8378	Approved
0.7308	Intermediate Similarity	NPD8380	Approved
0.7308	Intermediate Similarity	NPD8335	Approved
0.7308	Intermediate Similarity	NPD8379	Approved
0.7308	Intermediate Similarity	NPD8296	Approved
0.7302	Intermediate Similarity	NPD8133	Approved
0.728	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5141	Approved
0.72	Intermediate Similarity	NPD6371	Approved
0.7188	Intermediate Similarity	NPD6274	Approved
0.7167	Intermediate Similarity	NPD5286	Approved
0.7167	Intermediate Similarity	NPD4696	Approved
0.7167	Intermediate Similarity	NPD5285	Approved
0.7154	Intermediate Similarity	NPD7101	Approved
0.7154	Intermediate Similarity	NPD6008	Approved
0.7154	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD4755	Approved
0.7107	Intermediate Similarity	NPD5344	Discontinued
0.708	Intermediate Similarity	NPD7260	Phase 2
0.7077	Intermediate Similarity	NPD6335	Approved
0.7069	Intermediate Similarity	NPD6698	Approved
0.7069	Intermediate Similarity	NPD46	Approved
0.7049	Intermediate Similarity	NPD4633	Approved
0.7049	Intermediate Similarity	NPD5226	Approved
0.7049	Intermediate Similarity	NPD5224	Approved
0.7049	Intermediate Similarity	NPD5225	Approved
0.7034	Intermediate Similarity	NPD7748	Approved
0.7025	Intermediate Similarity	NPD4700	Approved
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.6992	Remote Similarity	NPD5174	Approved
0.6992	Remote Similarity	NPD5175	Approved
0.6967	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD3573	Approved
0.6953	Remote Similarity	NPD6053	Discontinued
0.695	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5778	Approved
0.6949	Remote Similarity	NPD5779	Approved
0.6947	Remote Similarity	NPD6314	Approved
0.6947	Remote Similarity	NPD6313	Approved
0.6923	Remote Similarity	NPD6868	Approved
0.6917	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5221	Approved
0.6917	Remote Similarity	NPD6909	Approved
0.6917	Remote Similarity	NPD5222	Approved
0.6917	Remote Similarity	NPD6908	Approved
0.6911	Remote Similarity	NPD7632	Discontinued
0.6906	Remote Similarity	NPD6845	Suspended
0.6905	Remote Similarity	NPD4729	Approved
0.6905	Remote Similarity	NPD4730	Approved
0.6884	Remote Similarity	NPD5956	Approved
0.688	Remote Similarity	NPD4768	Approved
0.688	Remote Similarity	NPD4767	Approved
0.6879	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7983	Approved
0.6864	Remote Similarity	NPD6411	Approved
0.6864	Remote Similarity	NPD6079	Approved
0.686	Remote Similarity	NPD5173	Approved
0.6838	Remote Similarity	NPD5328	Approved
0.6833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5695	Phase 3
0.6832	Remote Similarity	NPD7799	Discontinued
0.6807	Remote Similarity	NPD6399	Phase 3
0.6803	Remote Similarity	NPD5696	Approved
0.6803	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5250	Approved
0.6797	Remote Similarity	NPD5249	Phase 3
0.6797	Remote Similarity	NPD5251	Approved
0.6797	Remote Similarity	NPD5248	Approved
0.6797	Remote Similarity	NPD5247	Approved
0.6791	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4697	Phase 3
0.6772	Remote Similarity	NPD5128	Approved
0.6752	Remote Similarity	NPD6672	Approved
0.6752	Remote Similarity	NPD5737	Approved
0.675	Remote Similarity	NPD7900	Approved
0.675	Remote Similarity	NPD5282	Discontinued
0.675	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6648	Approved
0.6723	Remote Similarity	NPD5693	Phase 1
0.672	Remote Similarity	NPD4754	Approved
0.6695	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6101	Approved
0.6691	Remote Similarity	NPD6067	Discontinued
0.669	Remote Similarity	NPD8415	Approved
0.6647	Remote Similarity	NPD8407	Phase 2
0.6638	Remote Similarity	NPD1694	Approved
0.6615	Remote Similarity	NPD5216	Approved
0.6615	Remote Similarity	NPD5215	Approved
0.6615	Remote Similarity	NPD5217	Approved
0.6581	Remote Similarity	NPD3618	Phase 1
0.6566	Remote Similarity	NPD8368	Discontinued
0.6556	Remote Similarity	NPD7236	Approved
0.6555	Remote Similarity	NPD4753	Phase 2
0.6555	Remote Similarity	NPD6904	Approved
0.6555	Remote Similarity	NPD6673	Approved
0.6555	Remote Similarity	NPD6080	Approved
0.6552	Remote Similarity	NPD6333	Approved
0.6552	Remote Similarity	NPD6334	Approved
0.6538	Remote Similarity	NPD5169	Approved
0.6538	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5135	Approved
0.6529	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7839	Suspended
0.65	Remote Similarity	NPD5785	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.6496	Remote Similarity	NPD8080	Discontinued
0.6489	Remote Similarity	NPD5127	Approved
0.6471	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7239	Suspended
0.6449	Remote Similarity	NPD7829	Approved
0.6449	Remote Similarity	NPD7830	Approved
0.6449	Remote Similarity	NPD7642	Approved
0.6446	Remote Similarity	NPD7637	Suspended
0.6441	Remote Similarity	NPD5330	Approved
0.6441	Remote Similarity	NPD7334	Approved
0.6441	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6409	Approved
0.6441	Remote Similarity	NPD6684	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