NPASS Compound

Structure

NPC48647 OpenBabel07101718282D 35 38 0 0 1 0 0 0 0 0999 V2000 1.5180 -5.8564 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 -3.9641 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 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 -4.1622 0.0000 C 0 0 0 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 -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 -1.7321 -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 -0.8660 -1.5000 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 3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 2 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 1.5388 -0.5000 0.0000 C 0 0 2 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 2 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 2.2382 -2.4680 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 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 3.4743 -6.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 O 0 0 0 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 2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 5 29 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 18 2 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 31 1 0 0 0 0 19 9 1 6 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 29 1 6 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 28 4 1 6 0 0 0 29 30 1 6 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	526.615
LogP:	3.945
LogD:	2.874
LogS:	-3.962
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	5.16
Fsp3:	0.767
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:	-5.233
MDCK Permeability:	1.715452890493907e-05
Pgp-inhibitor:	0.312
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.135
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.333

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	92.02690887451172%
Volume Distribution (VD):	0.687
Pgp-substrate:	5.097325801849365%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	2.593
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.956
Carcinogencity:	0.028
Eye Corrosion:	0.008
Eye Irritation:	0.09
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: NPC48647

Natural Product ID:	NPC48647
*Common Name:**	3Alpha,16Alpha,26-Trihydroxylanosta-7,9(11),24-Trien-21-Oic Acid
IUPAC Name:	(E,2R)-2-[(3R,5R,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-7-hydroxy-6-methylhept-5-enoic acid
Synonyms:
Standard InCHIKey:	PJJIWWUPWPLBRE-XOSWQPBISA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-18(17-31)8-7-9-19(26(34)35)25-22(32)16-30(6)21-10-11-23-27(2,3)24(33)13-14-28(23,4)20(21)12-15-29(25,30)5/h8,10,12,19,22-25,31-33H,7,9,11,13-17H2,1-6H3,(H,34,35)/b18-8+/t19-,22-,23+,24-,25+,28-,29-,30+/m1/s1
SMILES:	OC/C(=C/CC[C@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC=C1C2=CC[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:	CHEMBL497711
PubChem CID:	16083191
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
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)91122-1]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[16933889]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27996259]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Activity	>	125.0	ug ml-1	PMID[468030]

☑ 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 NPC48647 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	170
0.1-0.2	949
0.2-0.3	4063
0.3-0.4	11284
0.4-0.5	11334
0.5-0.6	6872
0.6-0.7	5728
0.7-0.8	1962
0.8-0.85	245
0.85-0.9	60
0.9-0.95	22
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC186810
0.967	High Similarity	NPC162001
0.967	High Similarity	NPC45324
0.967	High Similarity	NPC222845
0.956	High Similarity	NPC469406
0.9362	High Similarity	NPC477813
0.9355	High Similarity	NPC155676
0.9341	High Similarity	NPC23434
0.9239	High Similarity	NPC152897
0.9239	High Similarity	NPC66429
0.9239	High Similarity	NPC470376
0.9239	High Similarity	NPC470375
0.913	High Similarity	NPC45269
0.9121	High Similarity	NPC84271
0.9121	High Similarity	NPC102414
0.9121	High Similarity	NPC77168
0.9043	High Similarity	NPC184848
0.9043	High Similarity	NPC69548
0.9043	High Similarity	NPC263347
0.9032	High Similarity	NPC243866
0.9022	High Similarity	NPC469400
0.9022	High Similarity	NPC46281
0.9011	High Similarity	NPC48866
0.9011	High Similarity	NPC247406
0.8958	High Similarity	NPC166745
0.8958	High Similarity	NPC235464
0.8936	High Similarity	NPC7165
0.8913	High Similarity	NPC155479
0.8913	High Similarity	NPC54689
0.8901	High Similarity	NPC159046
0.8901	High Similarity	NPC233836
0.8901	High Similarity	NPC187376
0.8901	High Similarity	NPC312215
0.8889	High Similarity	NPC477812
0.8878	High Similarity	NPC204450
0.8878	High Similarity	NPC195290
0.8854	High Similarity	NPC107243
0.883	High Similarity	NPC472942
0.883	High Similarity	NPC214697
0.8817	High Similarity	NPC123854
0.8817	High Similarity	NPC69622
0.8804	High Similarity	NPC242864
0.8804	High Similarity	NPC294480
0.8791	High Similarity	NPC55309
0.8791	High Similarity	NPC28252
0.8791	High Similarity	NPC212843
0.8788	High Similarity	NPC236390
0.875	High Similarity	NPC173272
0.8737	High Similarity	NPC49670
0.8723	High Similarity	NPC154101
0.8723	High Similarity	NPC297265
0.8723	High Similarity	NPC212948
0.871	High Similarity	NPC474704
0.871	High Similarity	NPC475921
0.8696	High Similarity	NPC474684
0.8696	High Similarity	NPC142361
0.8687	High Similarity	NPC293753
0.8687	High Similarity	NPC234892
0.8673	High Similarity	NPC154072
0.866	High Similarity	NPC320306
0.866	High Similarity	NPC469432
0.866	High Similarity	NPC475894
0.866	High Similarity	NPC57416
0.8646	High Similarity	NPC48330
0.8646	High Similarity	NPC20546
0.8617	High Similarity	NPC148414
0.8617	High Similarity	NPC175628
0.8617	High Similarity	NPC111585
0.8602	High Similarity	NPC183546
0.86	High Similarity	NPC55872
0.8587	High Similarity	NPC473226
0.8586	High Similarity	NPC99411
0.8571	High Similarity	NPC165064
0.8571	High Similarity	NPC10364
0.8571	High Similarity	NPC471717
0.8571	High Similarity	NPC197386
0.8557	High Similarity	NPC301534
0.8557	High Similarity	NPC250757
0.8557	High Similarity	NPC235053
0.8557	High Similarity	NPC472941
0.8557	High Similarity	NPC456
0.8529	High Similarity	NPC64844
0.8529	High Similarity	NPC42847
0.8526	High Similarity	NPC189520
0.8526	High Similarity	NPC107690
0.8526	High Similarity	NPC86266
0.8526	High Similarity	NPC212301
0.8526	High Similarity	NPC110657
0.8526	High Similarity	NPC26888
0.8515	High Similarity	NPC28656
0.8511	High Similarity	NPC472970
0.8511	High Similarity	NPC474889
0.8511	High Similarity	NPC472971
0.8511	High Similarity	NPC214387
0.85	High Similarity	NPC136289
0.8485	Intermediate Similarity	NPC327431
0.8485	Intermediate Similarity	NPC476274
0.8485	Intermediate Similarity	NPC287833
0.8485	Intermediate Similarity	NPC218383
0.8485	Intermediate Similarity	NPC205899
0.8485	Intermediate Similarity	NPC51370
0.8478	Intermediate Similarity	NPC474083
0.8469	Intermediate Similarity	NPC141401
0.8469	Intermediate Similarity	NPC122294
0.8469	Intermediate Similarity	NPC18319
0.8454	Intermediate Similarity	NPC318282
0.8454	Intermediate Similarity	NPC173875
0.8454	Intermediate Similarity	NPC469995
0.8454	Intermediate Similarity	NPC174948
0.8454	Intermediate Similarity	NPC53565
0.8454	Intermediate Similarity	NPC469599
0.8438	Intermediate Similarity	NPC107674
0.8438	Intermediate Similarity	NPC69454
0.8438	Intermediate Similarity	NPC470254
0.8438	Intermediate Similarity	NPC470224
0.8438	Intermediate Similarity	NPC170220
0.8438	Intermediate Similarity	NPC141497
0.8421	Intermediate Similarity	NPC477147
0.8421	Intermediate Similarity	NPC471896
0.8421	Intermediate Similarity	NPC477149
0.84	Intermediate Similarity	NPC302537
0.84	Intermediate Similarity	NPC476240
0.84	Intermediate Similarity	NPC224720
0.84	Intermediate Similarity	NPC81530
0.84	Intermediate Similarity	NPC163372
0.84	Intermediate Similarity	NPC476223
0.8387	Intermediate Similarity	NPC94755
0.8387	Intermediate Similarity	NPC469994
0.8387	Intermediate Similarity	NPC155011
0.8384	Intermediate Similarity	NPC16021
0.8384	Intermediate Similarity	NPC103051
0.8367	Intermediate Similarity	NPC7124
0.8367	Intermediate Similarity	NPC328371
0.8367	Intermediate Similarity	NPC249954
0.8367	Intermediate Similarity	NPC190713
0.8367	Intermediate Similarity	NPC95565
0.8352	Intermediate Similarity	NPC202389
0.8351	Intermediate Similarity	NPC471720
0.8351	Intermediate Similarity	NPC166906
0.8351	Intermediate Similarity	NPC111015
0.8351	Intermediate Similarity	NPC292793
0.8333	Intermediate Similarity	NPC63748
0.8333	Intermediate Similarity	NPC472228
0.8333	Intermediate Similarity	NPC233116
0.8333	Intermediate Similarity	NPC473998
0.8333	Intermediate Similarity	NPC472227
0.8317	Intermediate Similarity	NPC308726
0.8317	Intermediate Similarity	NPC119601
0.8317	Intermediate Similarity	NPC473424
0.8317	Intermediate Similarity	NPC477915
0.8317	Intermediate Similarity	NPC56498
0.8316	Intermediate Similarity	NPC262858
0.8316	Intermediate Similarity	NPC309603
0.8316	Intermediate Similarity	NPC472240
0.8316	Intermediate Similarity	NPC473999
0.8316	Intermediate Similarity	NPC2983
0.83	Intermediate Similarity	NPC144660
0.83	Intermediate Similarity	NPC266955
0.83	Intermediate Similarity	NPC307954
0.83	Intermediate Similarity	NPC299971
0.8298	Intermediate Similarity	NPC317590
0.8283	Intermediate Similarity	NPC253826
0.828	Intermediate Similarity	NPC471224
0.828	Intermediate Similarity	NPC474218
0.8269	Intermediate Similarity	NPC295244
0.8265	Intermediate Similarity	NPC127063
0.8265	Intermediate Similarity	NPC290481
0.8265	Intermediate Similarity	NPC470016
0.8265	Intermediate Similarity	NPC472932
0.8265	Intermediate Similarity	NPC259286
0.8265	Intermediate Similarity	NPC37646
0.8265	Intermediate Similarity	NPC271195
0.8265	Intermediate Similarity	NPC317586
0.8261	Intermediate Similarity	NPC310470
0.8261	Intermediate Similarity	NPC69279
0.8261	Intermediate Similarity	NPC83569
0.8252	Intermediate Similarity	NPC48733
0.8252	Intermediate Similarity	NPC319077
0.8252	Intermediate Similarity	NPC150531
0.8252	Intermediate Similarity	NPC97202
0.8252	Intermediate Similarity	NPC202167
0.8252	Intermediate Similarity	NPC296945
0.8252	Intermediate Similarity	NPC49958
0.8252	Intermediate Similarity	NPC323834
0.8252	Intermediate Similarity	NPC214264
0.8252	Intermediate Similarity	NPC302607
0.8252	Intermediate Similarity	NPC50692
0.8252	Intermediate Similarity	NPC476027
0.8252	Intermediate Similarity	NPC152695
0.8252	Intermediate Similarity	NPC260268
0.8252	Intermediate Similarity	NPC85829
0.8252	Intermediate Similarity	NPC171137
0.8247	Intermediate Similarity	NPC472930
0.8247	Intermediate Similarity	NPC206810
0.8235	Intermediate Similarity	NPC85742
0.8235	Intermediate Similarity	NPC140723
0.8229	Intermediate Similarity	NPC44240
0.8229	Intermediate Similarity	NPC18872
0.8229	Intermediate Similarity	NPC120968
0.8229	Intermediate Similarity	NPC210037

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 NPC48647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1236
0.2-0.3	3744
0.3-0.4	2678
0.4-0.5	814
0.5-0.6	199
0.6-0.7	190
0.7-0.8	143
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD5281	Approved
0.8333	Intermediate Similarity	NPD5284	Approved
0.8247	Intermediate Similarity	NPD6399	Phase 3
0.8077	Intermediate Similarity	NPD6675	Approved
0.8077	Intermediate Similarity	NPD7128	Approved
0.8077	Intermediate Similarity	NPD6402	Approved
0.8077	Intermediate Similarity	NPD5739	Approved
0.8061	Intermediate Similarity	NPD4202	Approved
0.8019	Intermediate Similarity	NPD6373	Approved
0.8019	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD3618	Phase 1
0.7979	Intermediate Similarity	NPD4786	Approved
0.7961	Intermediate Similarity	NPD5211	Phase 2
0.7941	Intermediate Similarity	NPD7640	Approved
0.7941	Intermediate Similarity	NPD7639	Approved
0.7938	Intermediate Similarity	NPD5328	Approved
0.7925	Intermediate Similarity	NPD7320	Approved
0.7925	Intermediate Similarity	NPD6899	Approved
0.7925	Intermediate Similarity	NPD6881	Approved
0.7921	Intermediate Similarity	NPD4755	Approved
0.7895	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6650	Approved
0.787	Intermediate Similarity	NPD6649	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.783	Intermediate Similarity	NPD5701	Approved
0.783	Intermediate Similarity	NPD5697	Approved
0.7812	Intermediate Similarity	NPD5279	Phase 3
0.781	Intermediate Similarity	NPD5141	Approved
0.7789	Intermediate Similarity	NPD3666	Approved
0.7789	Intermediate Similarity	NPD3133	Approved
0.7789	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD8035	Phase 2
0.7778	Intermediate Similarity	NPD8034	Phase 2
0.7778	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD6883	Approved
0.7778	Intermediate Similarity	NPD6079	Approved
0.7778	Intermediate Similarity	NPD7515	Phase 2
0.7778	Intermediate Similarity	NPD7290	Approved
0.7767	Intermediate Similarity	NPD5286	Approved
0.7767	Intermediate Similarity	NPD4700	Approved
0.7767	Intermediate Similarity	NPD4696	Approved
0.7767	Intermediate Similarity	NPD5285	Approved
0.7766	Intermediate Similarity	NPD3667	Approved
0.7757	Intermediate Similarity	NPD6011	Approved
0.7745	Intermediate Similarity	NPD6084	Phase 2
0.7745	Intermediate Similarity	NPD6083	Phase 2
0.7723	Intermediate Similarity	NPD5695	Phase 3
0.7706	Intermediate Similarity	NPD8130	Phase 1
0.7706	Intermediate Similarity	NPD6847	Approved
0.7706	Intermediate Similarity	NPD6617	Approved
0.7706	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD5223	Approved
0.7685	Intermediate Similarity	NPD6014	Approved
0.7685	Intermediate Similarity	NPD6012	Approved
0.7685	Intermediate Similarity	NPD6013	Approved
0.7647	Intermediate Similarity	NPD4697	Phase 3
0.7636	Intermediate Similarity	NPD8297	Approved
0.7636	Intermediate Similarity	NPD6882	Approved
0.7629	Intermediate Similarity	NPD7334	Approved
0.7629	Intermediate Similarity	NPD7521	Approved
0.7629	Intermediate Similarity	NPD4694	Approved
0.7629	Intermediate Similarity	NPD5330	Approved
0.7629	Intermediate Similarity	NPD7146	Approved
0.7629	Intermediate Similarity	NPD6409	Approved
0.7629	Intermediate Similarity	NPD6684	Approved
0.7629	Intermediate Similarity	NPD5280	Approved
0.7619	Intermediate Similarity	NPD5225	Approved
0.7619	Intermediate Similarity	NPD5224	Approved
0.7619	Intermediate Similarity	NPD4633	Approved
0.7619	Intermediate Similarity	NPD5226	Approved
0.76	Intermediate Similarity	NPD6050	Approved
0.7576	Intermediate Similarity	NPD4753	Phase 2
0.7573	Intermediate Similarity	NPD7902	Approved
0.7553	Intermediate Similarity	NPD7525	Registered
0.7549	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4754	Approved
0.7547	Intermediate Similarity	NPD5174	Approved
0.7547	Intermediate Similarity	NPD5175	Approved
0.7527	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD5362	Discontinued
0.75	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD5207	Approved
0.75	Intermediate Similarity	NPD5692	Phase 3
0.7476	Intermediate Similarity	NPD5221	Approved
0.7476	Intermediate Similarity	NPD5222	Approved
0.7476	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6903	Approved
0.7451	Intermediate Similarity	NPD7748	Approved
0.7429	Intermediate Similarity	NPD6404	Discontinued
0.7426	Intermediate Similarity	NPD5694	Approved
0.7426	Intermediate Similarity	NPD6411	Approved
0.7419	Intermediate Similarity	NPD6116	Phase 1
0.7411	Intermediate Similarity	NPD4632	Approved
0.7407	Intermediate Similarity	NPD4767	Approved
0.7407	Intermediate Similarity	NPD6008	Approved
0.7407	Intermediate Similarity	NPD4768	Approved
0.7404	Intermediate Similarity	NPD5173	Approved
0.7396	Intermediate Similarity	NPD4269	Approved
0.7396	Intermediate Similarity	NPD4270	Approved
0.7396	Intermediate Similarity	NPD4223	Phase 3
0.7396	Intermediate Similarity	NPD4221	Approved
0.7379	Intermediate Similarity	NPD5210	Approved
0.7379	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5778	Approved
0.7353	Intermediate Similarity	NPD5779	Approved
0.7347	Intermediate Similarity	NPD5329	Approved
0.7312	Intermediate Similarity	NPD6117	Approved
0.7312	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6335	Approved
0.73	Intermediate Similarity	NPD6672	Approved
0.73	Intermediate Similarity	NPD5737	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD7900	Approved
0.7282	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6274	Approved
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6098	Approved
0.7273	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD5128	Approved
0.7273	Intermediate Similarity	NPD5690	Phase 2
0.7273	Intermediate Similarity	NPD4730	Approved
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7245	Intermediate Similarity	NPD3668	Phase 3
0.7245	Intermediate Similarity	NPD4197	Approved
0.7241	Intermediate Similarity	NPD7100	Approved
0.7241	Intermediate Similarity	NPD7101	Approved
0.7228	Intermediate Similarity	NPD6904	Approved
0.7228	Intermediate Similarity	NPD6673	Approved
0.7228	Intermediate Similarity	NPD6051	Approved
0.7228	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6080	Approved
0.7228	Intermediate Similarity	NPD6101	Approved
0.7217	Intermediate Similarity	NPD6009	Approved
0.7217	Intermediate Similarity	NPD6317	Approved
0.7204	Intermediate Similarity	NPD7339	Approved
0.7204	Intermediate Similarity	NPD6942	Approved
0.72	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4822	Approved
0.7188	Intermediate Similarity	NPD4820	Approved
0.7188	Intermediate Similarity	NPD4252	Approved
0.7188	Intermediate Similarity	NPD4821	Approved
0.7188	Intermediate Similarity	NPD4819	Approved
0.7172	Intermediate Similarity	NPD5363	Approved
0.7158	Intermediate Similarity	NPD4268	Approved
0.7158	Intermediate Similarity	NPD6697	Approved
0.7158	Intermediate Similarity	NPD4271	Approved
0.7158	Intermediate Similarity	NPD6118	Approved
0.7158	Intermediate Similarity	NPD6115	Approved
0.7158	Intermediate Similarity	NPD6114	Approved
0.7157	Intermediate Similarity	NPD5785	Approved
0.7157	Intermediate Similarity	NPD4096	Approved
0.7155	Intermediate Similarity	NPD6313	Approved
0.7155	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5332	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5331	Approved
0.7143	Intermediate Similarity	NPD5250	Approved
0.7119	Intermediate Similarity	NPD6908	Approved
0.7119	Intermediate Similarity	NPD6909	Approved
0.7119	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6001	Approved
0.7113	Intermediate Similarity	NPD4692	Approved
0.7113	Intermediate Similarity	NPD4139	Approved
0.7113	Intermediate Similarity	NPD4790	Discontinued
0.71	Intermediate Similarity	NPD4693	Phase 3
0.71	Intermediate Similarity	NPD4690	Approved
0.71	Intermediate Similarity	NPD5205	Approved
0.71	Intermediate Similarity	NPD4689	Approved
0.71	Intermediate Similarity	NPD4688	Approved
0.71	Intermediate Similarity	NPD4138	Approved
0.71	Intermediate Similarity	NPD5786	Approved
0.7097	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5693	Phase 1
0.708	Intermediate Similarity	NPD5127	Approved
0.708	Intermediate Similarity	NPD5215	Approved
0.708	Intermediate Similarity	NPD5216	Approved
0.708	Intermediate Similarity	NPD5217	Approved
0.7059	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5654	Approved
0.7034	Intermediate Similarity	NPD6319	Approved
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7025	Intermediate Similarity	NPD7507	Approved
0.7021	Intermediate Similarity	NPD8264	Approved
0.7019	Intermediate Similarity	NPD5133	Approved
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.701	Intermediate Similarity	NPD4748	Discontinued
0.701	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5368	Approved
0.7009	Intermediate Similarity	NPD4225	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