NPASS Compound

Structure

CID52169 OpenBabel06191715392D 34 38 0 0 1 0 0 0 0 0999 V2000 1.8425 2.1505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4316 1.8344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0186 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0443 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -3.4103 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 1 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 -2.5315 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 -5.0979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 26 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 30 1 6 0 0 0 21 25 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.304
LogD:	1.062
LogS:	-2.258
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	4.782
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.436
MDCK Permeability:	2.769533784885425e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.166
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	54.609901428222656%
Volume Distribution (VD):	0.898
Pgp-substrate:	49.0557746887207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.283
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.51
CYP3A4-substrate:	0.386

ADMET: Excretion

Clearance (CL):	8.443
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.59
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.462
Maximum Recommended Daily Dose:	0.066
Skin Sensitization:	0.096
Carcinogencity:	0.517
Eye Corrosion:	0.034
Eye Irritation:	0.083
Respiratory Toxicity:	0.241

Download Data

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

Natural Product: NPC52169

Natural Product ID:	NPC52169
*Common Name:**	(2S,4Ar,6As,6Br,10S,12Ar,14Bs)-10-Hydroxy-2-(Hydroxymethyl)-2,6A,6B,9,9,12A-Hexamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-4A-Carboxylic Acid
IUPAC Name:	(2S,4aR,6aS,6bR,10S,12aR,14bS)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	CZWBKSDPBWNHGO-XZTHESQKSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-25(2)21-9-12-29(6)22(27(21,4)11-10-23(25)32)8-7-19-20-17-26(3,18-31)13-15-30(20,24(33)34)16-14-28(19,29)5/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21?,22?,23-,26-,27-,28+,29+,30-/m0/s1
SMILES:	CC1(C)C2CC[C@]3(C)C(CC=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]34C)C(=O)O)CO)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1733823
PubChem CID:	23641088
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
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	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
Potency	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[531587]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[531587]

☑ 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 NPC52169 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	201
0.1-0.2	1300
0.2-0.3	4922
0.3-0.4	14742
0.4-0.5	8600
0.5-0.6	5323
0.6-0.7	4749
0.7-0.8	2117
0.8-0.85	337
0.85-0.9	145
0.9-0.95	142
0.95-1	119

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC182797
0.988	High Similarity	NPC127689
0.988	High Similarity	NPC293048
0.988	High Similarity	NPC270768
0.988	High Similarity	NPC290972
0.988	High Similarity	NPC234346
0.988	High Similarity	NPC64872
0.988	High Similarity	NPC263393
0.988	High Similarity	NPC25906
0.988	High Similarity	NPC274330
0.988	High Similarity	NPC198664
0.988	High Similarity	NPC121798
0.988	High Similarity	NPC130520
0.988	High Similarity	NPC59263
0.988	High Similarity	NPC143232
0.988	High Similarity	NPC61543
0.988	High Similarity	NPC225585
0.9878	High Similarity	NPC18064
0.9878	High Similarity	NPC293564
0.9878	High Similarity	NPC98442
0.9878	High Similarity	NPC171203
0.9878	High Similarity	NPC88716
0.9878	High Similarity	NPC307426
0.9878	High Similarity	NPC142415
0.9878	High Similarity	NPC102683
0.9878	High Similarity	NPC68160
0.9878	High Similarity	NPC130577
0.9878	High Similarity	NPC51700
0.9878	High Similarity	NPC242468
0.9762	High Similarity	NPC126369
0.9762	High Similarity	NPC477872
0.9762	High Similarity	NPC7260
0.9762	High Similarity	NPC273621
0.9762	High Similarity	NPC130278
0.9762	High Similarity	NPC470589
0.9762	High Similarity	NPC120968
0.9762	High Similarity	NPC227467
0.9762	High Similarity	NPC290614
0.9762	High Similarity	NPC291028
0.9762	High Similarity	NPC18872
0.9762	High Similarity	NPC210037
0.9762	High Similarity	NPC111110
0.9759	High Similarity	NPC181225
0.9759	High Similarity	NPC246708
0.9759	High Similarity	NPC474512
0.9759	High Similarity	NPC470629
0.9759	High Similarity	NPC17733
0.9759	High Similarity	NPC40552
0.9759	High Similarity	NPC473242
0.9759	High Similarity	NPC290690
0.9756	High Similarity	NPC72638
0.9647	High Similarity	NPC235884
0.9647	High Similarity	NPC71074
0.9647	High Similarity	NPC187722
0.9647	High Similarity	NPC155120
0.9647	High Similarity	NPC472149
0.9647	High Similarity	NPC4036
0.9647	High Similarity	NPC306541
0.9647	High Similarity	NPC84319
0.9647	High Similarity	NPC233455
0.9647	High Similarity	NPC228784
0.9647	High Similarity	NPC158030
0.9647	High Similarity	NPC52021
0.9647	High Similarity	NPC474525
0.9647	High Similarity	NPC25299
0.9647	High Similarity	NPC324341
0.9647	High Similarity	NPC288833
0.9647	High Similarity	NPC300351
0.9647	High Similarity	NPC145067
0.9647	High Similarity	NPC282616
0.9647	High Similarity	NPC966
0.9647	High Similarity	NPC105189
0.9647	High Similarity	NPC65120
0.9643	High Similarity	NPC161751
0.9643	High Similarity	NPC470588
0.9643	High Similarity	NPC474972
0.9643	High Similarity	NPC95246
0.9535	High Similarity	NPC118519
0.9535	High Similarity	NPC74855
0.9535	High Similarity	NPC202728
0.9535	High Similarity	NPC307335
0.9535	High Similarity	NPC158059
0.9535	High Similarity	NPC214756
0.9535	High Similarity	NPC86368
0.9535	High Similarity	NPC298554
0.9535	High Similarity	NPC229281
0.9535	High Similarity	NPC136313
0.9535	High Similarity	NPC275809
0.9535	High Similarity	NPC272075
0.9535	High Similarity	NPC295643
0.9529	High Similarity	NPC86372
0.9529	High Similarity	NPC113989
0.9529	High Similarity	NPC474728
0.9529	High Similarity	NPC46441
0.9529	High Similarity	NPC172361
0.9529	High Similarity	NPC193750
0.9529	High Similarity	NPC120840
0.9529	High Similarity	NPC49320
0.9425	High Similarity	NPC6818
0.9425	High Similarity	NPC191412
0.9425	High Similarity	NPC263548
0.9425	High Similarity	NPC91010
0.9425	High Similarity	NPC474529
0.9425	High Similarity	NPC88116
0.9425	High Similarity	NPC282395
0.9425	High Similarity	NPC299996
0.9425	High Similarity	NPC114159
0.9425	High Similarity	NPC20235
0.9425	High Similarity	NPC222047
0.9425	High Similarity	NPC32407
0.9425	High Similarity	NPC159365
0.9425	High Similarity	NPC231063
0.9425	High Similarity	NPC145667
0.9425	High Similarity	NPC209868
0.9419	High Similarity	NPC475708
0.9419	High Similarity	NPC285184
0.9419	High Similarity	NPC471588
0.9419	High Similarity	NPC6255
0.9419	High Similarity	NPC77099
0.9419	High Similarity	NPC60755
0.9419	High Similarity	NPC38754
0.9419	High Similarity	NPC470590
0.9412	High Similarity	NPC474686
0.9412	High Similarity	NPC30522
0.9405	High Similarity	NPC71507
0.9398	High Similarity	NPC133954
0.9318	High Similarity	NPC474727
0.9318	High Similarity	NPC139570
0.9318	High Similarity	NPC148523
0.9318	High Similarity	NPC198245
0.9318	High Similarity	NPC96916
0.9318	High Similarity	NPC473240
0.931	High Similarity	NPC474436
0.931	High Similarity	NPC118490
0.931	High Similarity	NPC49776
0.931	High Similarity	NPC133579
0.931	High Similarity	NPC63118
0.931	High Similarity	NPC474806
0.9286	High Similarity	NPC95594
0.9286	High Similarity	NPC475862
0.9286	High Similarity	NPC73038
0.9286	High Similarity	NPC74363
0.9286	High Similarity	NPC213412
0.9286	High Similarity	NPC235341
0.9286	High Similarity	NPC477579
0.9277	High Similarity	NPC171789
0.9213	High Similarity	NPC157113
0.9213	High Similarity	NPC305464
0.9213	High Similarity	NPC259733
0.9213	High Similarity	NPC62516
0.9213	High Similarity	NPC230151
0.9213	High Similarity	NPC327179
0.9213	High Similarity	NPC132824
0.9213	High Similarity	NPC98874
0.9213	High Similarity	NPC19376
0.9213	High Similarity	NPC158371
0.9213	High Similarity	NPC116457
0.9213	High Similarity	NPC307282
0.9213	High Similarity	NPC204961
0.9213	High Similarity	NPC201657
0.9213	High Similarity	NPC173744
0.9213	High Similarity	NPC207922
0.9213	High Similarity	NPC73004
0.9213	High Similarity	NPC25848
0.9213	High Similarity	NPC476327
0.9213	High Similarity	NPC476318
0.9205	High Similarity	NPC296164
0.9205	High Similarity	NPC23621
0.9205	High Similarity	NPC184006
0.9205	High Similarity	NPC78580
0.9205	High Similarity	NPC80365
0.9205	High Similarity	NPC74751
0.9205	High Similarity	NPC60692
0.9205	High Similarity	NPC188102
0.9205	High Similarity	NPC87095
0.9195	High Similarity	NPC301244
0.9186	High Similarity	NPC281524
0.9176	High Similarity	NPC158141
0.9176	High Similarity	NPC73064
0.9176	High Similarity	NPC46912
0.9176	High Similarity	NPC173089
0.9176	High Similarity	NPC162107
0.9111	High Similarity	NPC106112
0.9111	High Similarity	NPC259788
0.9111	High Similarity	NPC187933
0.9111	High Similarity	NPC247139
0.9111	High Similarity	NPC261935
0.9111	High Similarity	NPC43686
0.9111	High Similarity	NPC189880
0.9111	High Similarity	NPC255589
0.9111	High Similarity	NPC476878
0.9111	High Similarity	NPC9613
0.9111	High Similarity	NPC476879
0.9101	High Similarity	NPC32118
0.9101	High Similarity	NPC83693
0.9101	High Similarity	NPC195715
0.9101	High Similarity	NPC290481
0.9101	High Similarity	NPC23241
0.907	High Similarity	NPC1753
0.907	High Similarity	NPC474511

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 NPC52169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1655
0.2-0.3	3854
0.3-0.4	2308
0.4-0.5	688
0.5-0.6	196
0.6-0.7	188
0.7-0.8	72
0.8-0.85	2
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9647	High Similarity	NPD7515	Phase 2
0.9205	High Similarity	NPD7748	Approved
0.8901	High Similarity	NPD7902	Approved
0.8721	High Similarity	NPD7520	Clinical (unspecified phase)
0.8571	High Similarity	NPD7900	Approved
0.8571	High Similarity	NPD7901	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7645	Phase 2
0.8202	Intermediate Similarity	NPD3618	Phase 1
0.8182	Intermediate Similarity	NPD4786	Approved
0.8161	Intermediate Similarity	NPD3667	Approved
0.8152	Intermediate Similarity	NPD8035	Phase 2
0.8152	Intermediate Similarity	NPD8034	Phase 2
0.8132	Intermediate Similarity	NPD5328	Approved
0.8065	Intermediate Similarity	NPD6399	Phase 3
0.7957	Intermediate Similarity	NPD6079	Approved
0.7935	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3666	Approved
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3133	Approved
0.7755	Intermediate Similarity	NPD7640	Approved
0.7755	Intermediate Similarity	NPD7639	Approved
0.7727	Intermediate Similarity	NPD7525	Registered
0.7723	Intermediate Similarity	NPD7128	Approved
0.7723	Intermediate Similarity	NPD6402	Approved
0.7723	Intermediate Similarity	NPD6675	Approved
0.7723	Intermediate Similarity	NPD5739	Approved
0.7684	Intermediate Similarity	NPD4202	Approved
0.7674	Intermediate Similarity	NPD6117	Approved
0.7629	Intermediate Similarity	NPD5222	Approved
0.7629	Intermediate Similarity	NPD5221	Approved
0.7629	Intermediate Similarity	NPD4697	Phase 3
0.7629	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6409	Approved
0.7609	Intermediate Similarity	NPD5330	Approved
0.7609	Intermediate Similarity	NPD6684	Approved
0.7609	Intermediate Similarity	NPD7521	Approved
0.7609	Intermediate Similarity	NPD7334	Approved
0.7609	Intermediate Similarity	NPD7146	Approved
0.7586	Intermediate Similarity	NPD6116	Phase 1
0.7582	Intermediate Similarity	NPD3668	Phase 3
0.7579	Intermediate Similarity	NPD6411	Approved
0.7573	Intermediate Similarity	NPD6881	Approved
0.7573	Intermediate Similarity	NPD6899	Approved
0.7573	Intermediate Similarity	NPD7320	Approved
0.7551	Intermediate Similarity	NPD6083	Phase 2
0.7551	Intermediate Similarity	NPD6084	Phase 2
0.7551	Intermediate Similarity	NPD4755	Approved
0.7551	Intermediate Similarity	NPD5173	Approved
0.7527	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.7476	Intermediate Similarity	NPD5701	Approved
0.7476	Intermediate Similarity	NPD5697	Approved
0.7449	Intermediate Similarity	NPD7614	Phase 1
0.7447	Intermediate Similarity	NPD6903	Approved
0.7447	Intermediate Similarity	NPD5737	Approved
0.7447	Intermediate Similarity	NPD6672	Approved
0.7442	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6883	Approved
0.7429	Intermediate Similarity	NPD7290	Approved
0.7429	Intermediate Similarity	NPD7102	Approved
0.7404	Intermediate Similarity	NPD6011	Approved
0.74	Intermediate Similarity	NPD5286	Approved
0.74	Intermediate Similarity	NPD4700	Approved
0.74	Intermediate Similarity	NPD4696	Approved
0.74	Intermediate Similarity	NPD5285	Approved
0.7368	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4753	Phase 2
0.7368	Intermediate Similarity	NPD6101	Approved
0.7358	Intermediate Similarity	NPD6649	Approved
0.7358	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8130	Phase 1
0.7358	Intermediate Similarity	NPD6869	Approved
0.7358	Intermediate Similarity	NPD6617	Approved
0.7358	Intermediate Similarity	NPD6650	Approved
0.7358	Intermediate Similarity	NPD6847	Approved
0.7356	Intermediate Similarity	NPD6942	Approved
0.7356	Intermediate Similarity	NPD7339	Approved
0.7333	Intermediate Similarity	NPD6014	Approved
0.7333	Intermediate Similarity	NPD6013	Approved
0.7333	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4695	Discontinued
0.7333	Intermediate Similarity	NPD6012	Approved
0.7327	Intermediate Similarity	NPD5223	Approved
0.729	Intermediate Similarity	NPD8297	Approved
0.729	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8328	Phase 3
0.7255	Intermediate Similarity	NPD5225	Approved
0.7255	Intermediate Similarity	NPD4633	Approved
0.7255	Intermediate Similarity	NPD5226	Approved
0.7255	Intermediate Similarity	NPD5224	Approved
0.7255	Intermediate Similarity	NPD5211	Phase 2
0.7234	Intermediate Similarity	NPD5279	Phase 3
0.7234	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4754	Approved
0.7184	Intermediate Similarity	NPD5174	Approved
0.7184	Intermediate Similarity	NPD5175	Approved
0.7182	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7115	Discovery
0.7174	Intermediate Similarity	NPD4221	Approved
0.7174	Intermediate Similarity	NPD4223	Phase 3
0.7172	Intermediate Similarity	NPD5695	Phase 3
0.7172	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5696	Approved
0.7128	Intermediate Similarity	NPD5329	Approved
0.7115	Intermediate Similarity	NPD5141	Approved
0.71	Intermediate Similarity	NPD7732	Phase 3
0.7097	Intermediate Similarity	NPD4788	Approved
0.7091	Intermediate Similarity	NPD6868	Approved
0.7087	Intermediate Similarity	NPD7632	Discontinued
0.7064	Intermediate Similarity	NPD4632	Approved
0.7053	Intermediate Similarity	NPD6098	Approved
0.7048	Intermediate Similarity	NPD4768	Approved
0.7048	Intermediate Similarity	NPD4767	Approved
0.7041	Intermediate Similarity	NPD5284	Approved
0.7041	Intermediate Similarity	NPD5281	Approved
0.7021	Intermediate Similarity	NPD4197	Approved
0.7011	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6673	Approved
0.701	Intermediate Similarity	NPD6904	Approved
0.701	Intermediate Similarity	NPD6080	Approved
0.7	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD5210	Approved
0.6989	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6412	Phase 2
0.6977	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5779	Approved
0.697	Remote Similarity	NPD5778	Approved
0.6964	Remote Similarity	NPD6335	Approved
0.6961	Remote Similarity	NPD4225	Approved
0.6937	Remote Similarity	NPD6274	Approved
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3617	Approved
0.6916	Remote Similarity	NPD4730	Approved
0.6916	Remote Similarity	NPD5128	Approved
0.6916	Remote Similarity	NPD5168	Approved
0.6916	Remote Similarity	NPD4729	Approved
0.6903	Remote Similarity	NPD7100	Approved
0.6903	Remote Similarity	NPD7101	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD4623	Approved
0.6875	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD5205	Approved
0.6875	Remote Similarity	NPD4138	Approved
0.6875	Remote Similarity	NPD4693	Phase 3
0.6875	Remote Similarity	NPD4519	Discontinued
0.6875	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD4689	Approved
0.6875	Remote Similarity	NPD4688	Approved
0.6875	Remote Similarity	NPD6009	Approved
0.6852	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6313	Approved
0.6814	Remote Similarity	NPD6314	Approved
0.6789	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5251	Approved
0.6789	Remote Similarity	NPD5169	Approved
0.6789	Remote Similarity	NPD5248	Approved
0.6789	Remote Similarity	NPD5250	Approved
0.6789	Remote Similarity	NPD4634	Approved
0.6789	Remote Similarity	NPD5135	Approved
0.6789	Remote Similarity	NPD5249	Phase 3
0.6789	Remote Similarity	NPD5247	Approved
0.6783	Remote Similarity	NPD6909	Approved
0.6783	Remote Similarity	NPD6908	Approved
0.6778	Remote Similarity	NPD3703	Phase 2
0.6774	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1694	Approved
0.6759	Remote Similarity	NPD6686	Approved
0.6757	Remote Similarity	NPD8133	Approved
0.6735	Remote Similarity	NPD5208	Approved
0.6733	Remote Similarity	NPD6001	Approved
0.6727	Remote Similarity	NPD5215	Approved
0.6727	Remote Similarity	NPD5127	Approved
0.6727	Remote Similarity	NPD5217	Approved
0.6727	Remote Similarity	NPD5216	Approved
0.6723	Remote Similarity	NPD7736	Approved
0.6705	Remote Similarity	NPD4244	Approved
0.6705	Remote Similarity	NPD4245	Approved
0.6701	Remote Similarity	NPD5280	Approved
0.6701	Remote Similarity	NPD5690	Phase 2
0.6701	Remote Similarity	NPD4694	Approved
0.67	Remote Similarity	NPD5693	Phase 1
0.67	Remote Similarity	NPD6050	Approved
0.6696	Remote Similarity	NPD6319	Approved
0.6695	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6638	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD6291	Clinical (unspecified phase)

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