NPASS Compound

Natural Product: NPC227744

Natural Product ID	NPC227744
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IACGAAXNDKIGSX-ZVAMACQUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21594139
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 84 88 0 0 0 0 0 0 0 0999 V2000 -5.1845 -3.1124 -0.0696 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0450 -1.7503 -0.7037 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8781 -1.7145 -1.9675 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6717 -0.7298 0.2568 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 0.5989 -0.0950 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6309 0.6212 0.4334 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8215 0.9632 1.9183 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4591 2.2053 1.9301 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9719 -0.6870 0.2211 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6248 -1.3802 -0.9877 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5031 -0.6195 0.0066 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7985 -1.7267 0.1038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6711 -1.8471 -0.0779 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3701 -0.5444 -0.2776 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8163 -0.5982 0.0886 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1357 -1.3563 1.3269 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5104 -1.3878 -1.0455 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9764 -1.5471 -0.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6922 -0.3157 -0.3838 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9212 0.7994 0.2519 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2757 0.9899 1.7000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4282 2.0770 -0.4575 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 2.0413 -1.8082 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4518 0.7665 -0.0277 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7005 1.8394 0.6733 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2526 1.8933 0.2521 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5761 0.5583 0.3787 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3353 0.3135 1.8335 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7721 0.6204 -0.3184 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5536 0.5738 -1.8409 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5341 1.8600 -0.0132 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 1.8038 -0.2179 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4145 1.8391 -1.5515 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7246 -0.6641 0.5243 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5110 -3.8466 -0.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2287 -3.4688 -0.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0100 -3.0641 1.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9214 -1.3479 -1.7588 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4258 -1.0256 -2.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0133 -2.7447 -2.3624 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7858 -0.7409 0.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4713 -1.1024 1.2577 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0306 0.6935 -1.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6487 1.4152 0.3874 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9039 0.9419 2.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5256 0.2619 2.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8929 2.9158 2.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2322 -1.3491 1.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0744 -2.2943 -1.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5657 -0.6886 -1.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3052 -2.6816 0.3414 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0292 -2.4071 0.8348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8131 -2.4893 -0.9922 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3497 -0.3353 -1.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5773 -1.1080 2.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0444 -2.4566 1.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2296 -1.2449 1.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4342 -0.8337 -2.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0738 -2.3913 -1.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4164 -2.0291 -1.6623 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0808 -2.3563 0.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2728 0.0111 -1.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0298 0.2328 2.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4468 0.9607 2.4037 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7995 1.9710 1.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5459 2.0348 -0.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1082 2.9875 0.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8760 2.6364 -2.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3632 1.0194 -1.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7493 1.8600 1.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1263 2.8293 0.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1071 2.3813 -0.7190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7483 2.5733 1.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2083 -0.7437 2.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1597 0.7988 2.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5747 0.8438 2.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4437 0.9873 -2.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2906 1.2020 -2.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4956 -0.4856 -2.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3471 2.2900 0.9923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1595 2.6710 -0.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4404 2.7118 0.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4023 2.7647 -1.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4517 -1.1432 0.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 7 8 1 0 6 9 1 0 9 10 1 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 19 34 1 0 10 2 1 0 29 11 1 0 32 6 1 0 27 14 1 0 24 15 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 7 45 1 0 7 46 1 0 8 47 1 0 9 48 1 1 10 49 1 0 10 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 14 54 1 6 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 19 62 1 6 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 24 69 1 6 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 28 75 1 0 28 76 1 0 30 77 1 0 30 78 1 0 30 79 1 0 31 80 1 0 31 81 1 0 32 82 1 1 33 83 1 0 34 84 1 0 M END

Standard InCHIKey	IACGAAXNDKIGSX-ZVAMACQUSA-N
Standard InCHI	InChI=1S/C30H50O4/c1-25(2)13-14-30(18-32)20(15-25)19-7-8-22-26(3)11-10-23(33)27(4,17-31)21(26)9-12-28(22,5)29(19,6)16-24(30)34/h7,20-24,31-34H,8-18H2,1-6H3/t20-,21+,22+,23-,24+,26-,27-,28+,29+,30+/m0/s1
SMILES	CC1(C)CC[C@@]2(CO)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	474.37	Volume:	517.178 ? Van der Waals volume.
Dense:	0.917	LogP:	3.647 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.6 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.544 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	80.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.421	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.035	Fsp³:	0.933
MCE-18:	104.897 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.526	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.436	Promiscuous compounds:	0.125

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.291	MDCK Permeability:	-4.92
Pgp-inhibitor:	0.005	Pgp-substrate:	0.026
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	0.357
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1.0	MRP1:	0.232
Plasma Protein Binding (PPB):	82.334%	Volume Distribution (VD):	-0.275
Fu:	15.188% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.976
OATP1B3 inhibitor:	0.0	BCRP inhibitor:	0.979
BSEP inhibitor:	0.962

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.252	CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.046
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.703
HLM stability:	0.043 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

7.382

Half-life (T1/2):

0.883

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.127
Human Hepatotoxicity (H-HT):	0.617	Drug-induced Liver Injury (DILI):	0.196
AMES Toxicity:	0.528	Rat Oral Acute Toxicity:	0.708
Maximum Recommended Daily Dose:	0.448	Skin Sensitization:	0.997
Carcinogencity:	0.971	Eye Corrosion:	0.002
Eye Irritation:	0.312	Respiratory Toxicity:	0.909
Drug-induced Neurotoxicity:	0.136	Ototoxicity:	0.621
Hematotoxicity:	0.75	Drug-induced Nephrotoxicity:	0.831
Genotoxicity:	0.485	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.948	Hek293 Cytotoxicity:	0.666
BCF:	1.564 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.766 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.371 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.554 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1248/cpb.36.2220]
NPO25189	Stephania epigaea	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23621840]
NPO5612	Synoicum pulmonaria	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24547899]
NPO5612	Synoicum pulmonaria	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12290	Euphydryas cynthia	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24398	Diospyros japonica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25125	Libocedrus plumosa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25062	Genista cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3692	Dolichopentas longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25062	Genista cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24398	Diospyros japonica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24806	Alectra parasitica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5612	Synoicum pulmonaria	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25125	Libocedrus plumosa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24747	Targionia hypophylla	Species	Targioniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18670	Adiantum malesianum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23640	Gynoxys nitida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12290	Euphydryas cynthia	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25189	Stephania epigaea	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25156	Ruellia rosea	Species	Acanthaceae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC227744 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	29093
0.1-0.2	17459
0.2-0.3	2427
0.3-0.4	679
0.4-0.5	148
0.5-0.6	29
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8519	High Similarity	NPC253807
0.8519	High Similarity	NPC158662
0.7679	Intermediate Similarity	NPC196753
0.7119	Intermediate Similarity	NPC230295
0.7119	Intermediate Similarity	NPC253402
0.7119	Intermediate Similarity	NPC98386
0.6833	Remote Similarity	NPC53744
0.678	Remote Similarity	NPC311078
0.678	Remote Similarity	NPC34177
0.65	Remote Similarity	NPC101475
0.6406	Remote Similarity	NPC213412
0.6271	Remote Similarity	NPC290598
0.6271	Remote Similarity	NPC30590
0.6143	Remote Similarity	NPC86368
0.6129	Remote Similarity	NPC235341
0.6129	Remote Similarity	NPC480924
0.6061	Remote Similarity	NPC488519
0.6032	Remote Similarity	NPC159168
0.5873	Remote Similarity	NPC478657
0.5833	Remote Similarity	NPC258547
0.5821	Remote Similarity	NPC270768
0.5821	Remote Similarity	NPC59263
0.5821	Remote Similarity	NPC210106
0.5606	Remote Similarity	NPC246708
0.5584	Remote Similarity	NPC237503
0.5571	Remote Similarity	NPC263393
0.5556	Remote Similarity	NPC474989
0.5362	Remote Similarity	NPC229281
0.5362	Remote Similarity	NPC121798
0.5362	Remote Similarity	NPC234346
0.5352	Remote Similarity	NPC191412
0.5352	Remote Similarity	NPC114159
0.5352	Remote Similarity	NPC6818
0.5303	Remote Similarity	NPC238992
0.5286	Remote Similarity	NPC61543
0.5286	Remote Similarity	NPC293048
0.5286	Remote Similarity	NPC225585
0.5278	Remote Similarity	NPC294360
0.5224	Remote Similarity	NPC480950
0.5205	Remote Similarity	NPC116457
0.5075	Remote Similarity	NPC237795
0.5075	Remote Similarity	NPC470588
0.5075	Remote Similarity	NPC82538
0.5075	Remote Similarity	NPC3915
0.5068	Remote Similarity	NPC127689
0.5068	Remote Similarity	NPC130520
0.5067	Remote Similarity	NPC283343

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC227744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8274
0.1-0.2	852
0.2-0.3	22
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6308	Remote Similarity	NPD7645	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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