NPASS Compound

Structure

CID329417 OpenBabel06191716212D 35 38 0 0 1 0 0 0 0 0999 V2000 -5.4701 -1.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9049 -0.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8835 -3.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4709 -0.5101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0218 -3.3052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.9505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8236 -1.4260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3183 -2.6862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8237 1.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2940 1.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2940 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6461 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5409 -1.5847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2476 -2.4883 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6473 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8236 0.4755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4709 1.4265 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6473 1.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1171 1.4265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1170 0.4754 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6461 -0.9504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6824 -1.9803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8237 -1.4259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4709 0.4755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8240 -2.3760 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 1.6473 2.8876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9707 1.9191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9706 -0.0172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4998 -1.4429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9757 -1.0767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1181 -3.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 26 1 0 0 0 0 9 15 1 0 0 0 0 9 23 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 12 25 1 0 0 0 0 13 22 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 1 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 29 2 0 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 31 1 1 0 0 0 22 24 1 0 0 0 0 22 32 1 1 0 0 0 23 27 1 0 0 0 0 23 33 1 1 0 0 0 24 26 1 1 0 0 0 24 27 1 0 0 0 0 25 4 1 1 0 0 0 26 28 1 1 0 0 0 27 6 1 6 0 0 0 27 34 1 0 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.32
Volume:	514.877
LogP:	2.14
LogD:	1.271
LogS:	-3.561
# Rotatable Bonds:	5
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	5.599
Fsp3:	0.893
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:	-5.172
MDCK Permeability:	4.2410215428390075e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.572
30% Bioavailability (F30%):	0.187

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	70.538818359375%
Volume Distribution (VD):	1.011
Pgp-substrate:	14.71120548248291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.257
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.698
CYP3A4-substrate:	0.74

ADMET: Excretion

Clearance (CL):	2.94
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.336
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.296
Carcinogencity:	0.026
Eye Corrosion:	0.01
Eye Irritation:	0.031
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC329417

Natural Product ID:	NPC329417
*Common Name:**	Polyporoid C
IUPAC Name:	(2S,3R,5R,9R,10R,13R,14S,16S,17R)-17-[(2R,3R)-2,3-dihydroxy-5,6-dimethylheptan-2-yl]-2,3,14,16-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	Polyporoid C
Standard InCHIKey:	RVRAYMBCPTYQKZ-UFOPSCFWSA-N
Standard InCHI:	InChI=1S/C28H46O7/c1-14(2)15(3)9-23(33)27(6,34)24-22(32)13-28(35)17-10-19(29)18-11-20(30)21(31)12-25(18,4)16(17)7-8-26(24,28)5/h10,14-16,18,20-24,30-35H,7-9,11-13H2,1-6H3/t15?,16-,18-,20+,21-,22-,23+,24-,25+,26+,27-,28+/m0/s1
SMILES:	CC(C)C(C)CC(C(C)(C1C(CC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL411238
PubChem CID:	44449996
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols 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
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.184	uM	PMID[497438]

☑ 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 NPC329417 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	208
0.1-0.2	1328
0.2-0.3	4467
0.3-0.4	8461
0.4-0.5	12724
0.5-0.6	6589
0.6-0.7	6057
0.7-0.8	2552
0.8-0.85	238
0.85-0.9	31
0.9-0.95	14
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC83744
0.9798	High Similarity	NPC202167
0.9798	High Similarity	NPC260268
0.9798	High Similarity	NPC171137
0.9798	High Similarity	NPC152695
0.9798	High Similarity	NPC85829
0.9798	High Similarity	NPC302607
0.9798	High Similarity	NPC97202
0.9798	High Similarity	NPC50692
0.9798	High Similarity	NPC319077
0.9798	High Similarity	NPC48733
0.9798	High Similarity	NPC150531
0.9798	High Similarity	NPC49958
0.9798	High Similarity	NPC214264
0.9798	High Similarity	NPC296945
0.9798	High Similarity	NPC476027
0.97	High Similarity	NPC220229
0.97	High Similarity	NPC477916
0.97	High Similarity	NPC475060
0.9697	High Similarity	NPC204833
0.9697	High Similarity	NPC209502
0.9604	High Similarity	NPC217201
0.96	High Similarity	NPC149047
0.951	High Similarity	NPC11710
0.9495	High Similarity	NPC477915
0.9429	High Similarity	NPC326542
0.9423	High Similarity	NPC207251
0.9333	High Similarity	NPC317210
0.9333	High Similarity	NPC73300
0.9333	High Similarity	NPC108721
0.9293	High Similarity	NPC154072
0.9231	High Similarity	NPC76084
0.9223	High Similarity	NPC65941
0.9151	High Similarity	NPC250109
0.9151	High Similarity	NPC962
0.9135	High Similarity	NPC214644
0.902	High Similarity	NPC191892
0.8981	High Similarity	NPC49492
0.8981	High Similarity	NPC266728
0.8922	High Similarity	NPC473424
0.8889	High Similarity	NPC271195
0.8846	High Similarity	NPC257353
0.8846	High Similarity	NPC323834
0.8788	High Similarity	NPC111015
0.8762	High Similarity	NPC165873
0.8739	High Similarity	NPC475041
0.8713	High Similarity	NPC18509
0.8673	High Similarity	NPC28532
0.8673	High Similarity	NPC222688
0.8667	High Similarity	NPC166607
0.8661	High Similarity	NPC109973
0.8654	High Similarity	NPC247957
0.8654	High Similarity	NPC249187
0.8654	High Similarity	NPC117185
0.8654	High Similarity	NPC311612
0.8614	High Similarity	NPC249954
0.8614	High Similarity	NPC49371
0.86	High Similarity	NPC196227
0.8585	High Similarity	NPC185
0.8571	High Similarity	NPC75531
0.8571	High Similarity	NPC160843
0.8571	High Similarity	NPC149124
0.8571	High Similarity	NPC72255
0.8559	High Similarity	NPC471854
0.8558	High Similarity	NPC87351
0.8544	High Similarity	NPC144956
0.8529	High Similarity	NPC190554
0.8519	High Similarity	NPC235077
0.8515	High Similarity	NPC259286
0.8515	High Similarity	NPC472932
0.8515	High Similarity	NPC200702
0.8515	High Similarity	NPC473170
0.8509	High Similarity	NPC269642
0.85	High Similarity	NPC472930
0.85	High Similarity	NPC69454
0.85	High Similarity	NPC472496
0.8476	Intermediate Similarity	NPC55872
0.8447	Intermediate Similarity	NPC103051
0.8431	Intermediate Similarity	NPC471463
0.8416	Intermediate Similarity	NPC472976
0.8416	Intermediate Similarity	NPC472977
0.8416	Intermediate Similarity	NPC280804
0.8416	Intermediate Similarity	NPC8993
0.8411	Intermediate Similarity	NPC43285
0.8411	Intermediate Similarity	NPC58370
0.8411	Intermediate Similarity	NPC144459
0.84	Intermediate Similarity	NPC155304
0.84	Intermediate Similarity	NPC233116
0.84	Intermediate Similarity	NPC116726
0.84	Intermediate Similarity	NPC472978
0.84	Intermediate Similarity	NPC475806
0.84	Intermediate Similarity	NPC473998
0.84	Intermediate Similarity	NPC63748
0.8396	Intermediate Similarity	NPC28656
0.8384	Intermediate Similarity	NPC477943
0.8384	Intermediate Similarity	NPC309603
0.8384	Intermediate Similarity	NPC473999
0.8381	Intermediate Similarity	NPC22388
0.8381	Intermediate Similarity	NPC204450
0.8381	Intermediate Similarity	NPC195290
0.8365	Intermediate Similarity	NPC474720
0.8365	Intermediate Similarity	NPC316964
0.8365	Intermediate Similarity	NPC15390
0.8365	Intermediate Similarity	NPC218383
0.8365	Intermediate Similarity	NPC83709
0.8365	Intermediate Similarity	NPC110149
0.8364	Intermediate Similarity	NPC280782
0.835	Intermediate Similarity	NPC474938
0.835	Intermediate Similarity	NPC474785
0.8333	Intermediate Similarity	NPC472824
0.8333	Intermediate Similarity	NPC472485
0.8319	Intermediate Similarity	NPC311554
0.8319	Intermediate Similarity	NPC257457
0.8318	Intermediate Similarity	NPC60681
0.8317	Intermediate Similarity	NPC109305
0.8304	Intermediate Similarity	NPC196931
0.8302	Intermediate Similarity	NPC236390
0.8302	Intermediate Similarity	NPC26478
0.8302	Intermediate Similarity	NPC111323
0.83	Intermediate Similarity	NPC48010
0.83	Intermediate Similarity	NPC136801
0.83	Intermediate Similarity	NPC100313
0.83	Intermediate Similarity	NPC134321
0.8283	Intermediate Similarity	NPC328539
0.8283	Intermediate Similarity	NPC470417
0.8276	Intermediate Similarity	NPC473979
0.8257	Intermediate Similarity	NPC470257
0.8252	Intermediate Similarity	NPC117133
0.8246	Intermediate Similarity	NPC61520
0.8235	Intermediate Similarity	NPC103527
0.8235	Intermediate Similarity	NPC245972
0.8235	Intermediate Similarity	NPC196485
0.823	Intermediate Similarity	NPC218970
0.8224	Intermediate Similarity	NPC477812
0.8224	Intermediate Similarity	NPC471293
0.822	Intermediate Similarity	NPC470882
0.8218	Intermediate Similarity	NPC185936
0.8218	Intermediate Similarity	NPC168027
0.8208	Intermediate Similarity	NPC136289
0.8208	Intermediate Similarity	NPC293753
0.8208	Intermediate Similarity	NPC234892
0.8208	Intermediate Similarity	NPC185530
0.82	Intermediate Similarity	NPC77263
0.82	Intermediate Similarity	NPC31985
0.82	Intermediate Similarity	NPC86319
0.82	Intermediate Similarity	NPC32830
0.82	Intermediate Similarity	NPC2983
0.82	Intermediate Similarity	NPC250592
0.82	Intermediate Similarity	NPC1015
0.82	Intermediate Similarity	NPC275740
0.82	Intermediate Similarity	NPC472973
0.82	Intermediate Similarity	NPC186688
0.8198	Intermediate Similarity	NPC472002
0.819	Intermediate Similarity	NPC476274
0.819	Intermediate Similarity	NPC107493
0.8182	Intermediate Similarity	NPC90652
0.8174	Intermediate Similarity	NPC79579
0.8173	Intermediate Similarity	NPC170978
0.8173	Intermediate Similarity	NPC320306
0.8173	Intermediate Similarity	NPC107243
0.8165	Intermediate Similarity	NPC472218
0.8165	Intermediate Similarity	NPC472825
0.8165	Intermediate Similarity	NPC177064
0.8165	Intermediate Similarity	NPC472217
0.8165	Intermediate Similarity	NPC472219
0.8158	Intermediate Similarity	NPC329736
0.8158	Intermediate Similarity	NPC153440
0.8155	Intermediate Similarity	NPC297199
0.8155	Intermediate Similarity	NPC53565
0.8155	Intermediate Similarity	NPC266899
0.8155	Intermediate Similarity	NPC272617
0.8155	Intermediate Similarity	NPC180950
0.8151	Intermediate Similarity	NPC473888
0.8142	Intermediate Similarity	NPC148458
0.8137	Intermediate Similarity	NPC470376
0.8137	Intermediate Similarity	NPC474736
0.8137	Intermediate Similarity	NPC475255
0.8137	Intermediate Similarity	NPC470375
0.8136	Intermediate Similarity	NPC293112
0.8131	Intermediate Similarity	NPC140723
0.8125	Intermediate Similarity	NPC194100
0.8125	Intermediate Similarity	NPC52634
0.8125	Intermediate Similarity	NPC178981
0.812	Intermediate Similarity	NPC469789
0.8119	Intermediate Similarity	NPC128672
0.8119	Intermediate Similarity	NPC473099
0.8119	Intermediate Similarity	NPC320026
0.8119	Intermediate Similarity	NPC171441
0.8113	Intermediate Similarity	NPC476240
0.8113	Intermediate Similarity	NPC81530
0.8113	Intermediate Similarity	NPC476223
0.8113	Intermediate Similarity	NPC472924
0.8113	Intermediate Similarity	NPC471401
0.8113	Intermediate Similarity	NPC302537
0.8113	Intermediate Similarity	NPC224720
0.8113	Intermediate Similarity	NPC476897
0.8113	Intermediate Similarity	NPC163372
0.8103	Intermediate Similarity	NPC46570
0.81	Intermediate Similarity	NPC474668
0.81	Intermediate Similarity	NPC131470

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 NPC329417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1624
0.2-0.3	3997
0.3-0.4	2224
0.4-0.5	643
0.5-0.6	169
0.6-0.7	154
0.7-0.8	110
0.8-0.85	42
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8738	High Similarity	NPD5211	Phase 2
0.8713	High Similarity	NPD4755	Approved
0.8571	High Similarity	NPD5141	Approved
0.8544	High Similarity	NPD5285	Approved
0.8544	High Similarity	NPD5286	Approved
0.8544	High Similarity	NPD4700	Approved
0.8544	High Similarity	NPD4696	Approved
0.8519	High Similarity	NPD4634	Approved
0.8384	Intermediate Similarity	NPD5328	Approved
0.8381	Intermediate Similarity	NPD5226	Approved
0.8381	Intermediate Similarity	NPD4633	Approved
0.8381	Intermediate Similarity	NPD5225	Approved
0.8381	Intermediate Similarity	NPD5224	Approved
0.8318	Intermediate Similarity	NPD6675	Approved
0.8318	Intermediate Similarity	NPD5739	Approved
0.8318	Intermediate Similarity	NPD7128	Approved
0.8318	Intermediate Similarity	NPD6402	Approved
0.8317	Intermediate Similarity	NPD4202	Approved
0.8302	Intermediate Similarity	NPD5175	Approved
0.8302	Intermediate Similarity	NPD5174	Approved
0.8286	Intermediate Similarity	NPD5223	Approved
0.8257	Intermediate Similarity	NPD6372	Approved
0.8257	Intermediate Similarity	NPD6373	Approved
0.8218	Intermediate Similarity	NPD6079	Approved
0.8165	Intermediate Similarity	NPD6881	Approved
0.8165	Intermediate Similarity	NPD7320	Approved
0.8165	Intermediate Similarity	NPD6899	Approved
0.8148	Intermediate Similarity	NPD4768	Approved
0.8148	Intermediate Similarity	NPD4767	Approved
0.8131	Intermediate Similarity	NPD4754	Approved
0.8125	Intermediate Similarity	NPD4632	Approved
0.8108	Intermediate Similarity	NPD6649	Approved
0.8108	Intermediate Similarity	NPD6650	Approved
0.8081	Intermediate Similarity	NPD3618	Phase 1
0.8077	Intermediate Similarity	NPD4697	Phase 3
0.8073	Intermediate Similarity	NPD5701	Approved
0.8073	Intermediate Similarity	NPD5697	Approved
0.8036	Intermediate Similarity	NPD8297	Approved
0.802	Intermediate Similarity	NPD4753	Phase 2
0.8018	Intermediate Similarity	NPD7290	Approved
0.8018	Intermediate Similarity	NPD6883	Approved
0.8018	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD5128	Approved
0.8	Intermediate Similarity	NPD4729	Approved
0.8	Intermediate Similarity	NPD4730	Approved
0.7946	Intermediate Similarity	NPD6869	Approved
0.7946	Intermediate Similarity	NPD6847	Approved
0.7946	Intermediate Similarity	NPD8130	Phase 1
0.7946	Intermediate Similarity	NPD6617	Approved
0.7928	Intermediate Similarity	NPD6013	Approved
0.7928	Intermediate Similarity	NPD6014	Approved
0.7928	Intermediate Similarity	NPD6012	Approved
0.7905	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5222	Approved
0.7905	Intermediate Similarity	NPD5221	Approved
0.7879	Intermediate Similarity	NPD3133	Approved
0.7879	Intermediate Similarity	NPD3665	Phase 1
0.7879	Intermediate Similarity	NPD3666	Approved
0.7876	Intermediate Similarity	NPD6882	Approved
0.7863	Intermediate Similarity	NPD6319	Approved
0.7863	Intermediate Similarity	NPD6054	Approved
0.7863	Intermediate Similarity	NPD6059	Approved
0.7857	Intermediate Similarity	NPD5247	Approved
0.7857	Intermediate Similarity	NPD5251	Approved
0.7857	Intermediate Similarity	NPD5248	Approved
0.7857	Intermediate Similarity	NPD5249	Phase 3
0.7857	Intermediate Similarity	NPD5250	Approved
0.7838	Intermediate Similarity	NPD6011	Approved
0.783	Intermediate Similarity	NPD5173	Approved
0.7818	Intermediate Similarity	NPD6008	Approved
0.781	Intermediate Similarity	NPD5210	Approved
0.781	Intermediate Similarity	NPD4629	Approved
0.7788	Intermediate Similarity	NPD5216	Approved
0.7788	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5217	Approved
0.7788	Intermediate Similarity	NPD5215	Approved
0.7759	Intermediate Similarity	NPD6009	Approved
0.7759	Intermediate Similarity	NPD7115	Discovery
0.7748	Intermediate Similarity	NPD6412	Phase 2
0.7731	Intermediate Similarity	NPD6370	Approved
0.77	Intermediate Similarity	NPD4786	Approved
0.7699	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD5135	Approved
0.7699	Intermediate Similarity	NPD5169	Approved
0.7686	Intermediate Similarity	NPD7507	Approved
0.7685	Intermediate Similarity	NPD7640	Approved
0.7685	Intermediate Similarity	NPD7639	Approved
0.7677	Intermediate Similarity	NPD4223	Phase 3
0.7677	Intermediate Similarity	NPD4221	Approved
0.7664	Intermediate Similarity	NPD6084	Phase 2
0.7664	Intermediate Similarity	NPD6083	Phase 2
0.7647	Intermediate Similarity	NPD6015	Approved
0.7647	Intermediate Similarity	NPD6016	Approved
0.7632	Intermediate Similarity	NPD5127	Approved
0.7624	Intermediate Similarity	NPD5329	Approved
0.7603	Intermediate Similarity	NPD7492	Approved
0.7593	Intermediate Similarity	NPD7638	Approved
0.7583	Intermediate Similarity	NPD5988	Approved
0.7549	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6616	Approved
0.7525	Intermediate Similarity	NPD4197	Approved
0.7521	Intermediate Similarity	NPD6274	Approved
0.7521	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD3667	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7479	Intermediate Similarity	NPD7100	Approved
0.7479	Intermediate Similarity	NPD7101	Approved
0.7453	Intermediate Similarity	NPD6399	Phase 3
0.7436	Intermediate Similarity	NPD5167	Approved
0.7431	Intermediate Similarity	NPD5696	Approved
0.7419	Intermediate Similarity	NPD7736	Approved
0.7414	Intermediate Similarity	NPD6053	Discontinued
0.7398	Intermediate Similarity	NPD6336	Discontinued
0.7395	Intermediate Similarity	NPD6335	Approved
0.7379	Intermediate Similarity	NPD4138	Approved
0.7379	Intermediate Similarity	NPD5205	Approved
0.7379	Intermediate Similarity	NPD4690	Approved
0.7379	Intermediate Similarity	NPD4693	Phase 3
0.7379	Intermediate Similarity	NPD4688	Approved
0.7379	Intermediate Similarity	NPD4689	Approved
0.7358	Intermediate Similarity	NPD5281	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7358	Intermediate Similarity	NPD5284	Approved
0.7355	Intermediate Similarity	NPD6908	Approved
0.7355	Intermediate Similarity	NPD6909	Approved
0.7315	Intermediate Similarity	NPD5695	Phase 3
0.7315	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6317	Approved
0.7308	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7525	Registered
0.728	Intermediate Similarity	NPD6033	Approved
0.7255	Intermediate Similarity	NPD4788	Approved
0.725	Intermediate Similarity	NPD6313	Approved
0.725	Intermediate Similarity	NPD6314	Approved
0.7217	Intermediate Similarity	NPD5168	Approved
0.7213	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6409	Approved
0.7212	Intermediate Similarity	NPD6684	Approved
0.7212	Intermediate Similarity	NPD7146	Approved
0.7212	Intermediate Similarity	NPD5330	Approved
0.7212	Intermediate Similarity	NPD7521	Approved
0.7212	Intermediate Similarity	NPD7334	Approved
0.7212	Intermediate Similarity	NPD5279	Phase 3
0.7212	Intermediate Similarity	NPD4694	Approved
0.7212	Intermediate Similarity	NPD5690	Phase 2
0.7212	Intermediate Similarity	NPD5280	Approved
0.719	Intermediate Similarity	NPD4522	Approved
0.719	Intermediate Similarity	NPD7516	Approved
0.7182	Intermediate Similarity	NPD7902	Approved
0.7107	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD7328	Approved
0.7094	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7632	Discontinued
0.7075	Intermediate Similarity	NPD6903	Approved
0.7075	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8033	Approved
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7748	Approved
0.7048	Intermediate Similarity	NPD4623	Approved
0.7048	Intermediate Similarity	NPD4519	Discontinued
0.703	Intermediate Similarity	NPD4195	Approved
0.7019	Intermediate Similarity	NPD3668	Phase 3
0.7009	Intermediate Similarity	NPD6080	Approved
0.7009	Intermediate Similarity	NPD6904	Approved
0.7009	Intermediate Similarity	NPD6673	Approved
0.6992	Remote Similarity	NPD8377	Approved
0.6992	Remote Similarity	NPD8294	Approved
0.6981	Remote Similarity	NPD7524	Approved
0.6964	Remote Similarity	NPD4225	Approved
0.696	Remote Similarity	NPD6067	Discontinued
0.696	Remote Similarity	NPD8328	Phase 3
0.6952	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6868	Approved
0.6935	Remote Similarity	NPD8296	Approved
0.6935	Remote Similarity	NPD8378	Approved
0.6935	Remote Similarity	NPD8335	Approved
0.6935	Remote Similarity	NPD8380	Approved
0.6935	Remote Similarity	NPD7503	Approved
0.6935	Remote Similarity	NPD8379	Approved
0.6923	Remote Similarity	NPD6686	Approved
0.6916	Remote Similarity	NPD5737	Approved
0.6916	Remote Similarity	NPD6672	Approved
0.6909	Remote Similarity	NPD6001	Approved
0.6909	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7900	Approved
0.69	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8035	Phase 2
0.6881	Remote Similarity	NPD8034	Phase 2
0.6881	Remote Similarity	NPD5693	Phase 1
0.6864	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6371	Approved
0.68	Remote Similarity	NPD6942	Approved
0.68	Remote Similarity	NPD3703	Phase 2
0.68	Remote Similarity	NPD7339	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